Esters-buliding-blocks

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 148547-19-7 as follows. 148547-19-7

Step A. Methyl 2,2′-dimethyl-1,1′-biphenyl-4-carboxylate A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane/water (300 mL:200 mL) was purged with nitrogen for 1 hour. [1,-bis(Diphenylphosphino) ferrocene]dichloropalladium [II] (4.5 g, 5.5 mmol) was added. The reaction mixture was heated to 100 C. with vigorous stirring for 3.5 hours, then cooled and filtered through Celitee (Celite Corp., Santa Barbara, Calif.). The cake was washed with ethyl acetate (500 mL). The combined organic phases were washed with 1N sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate, and concentrated in vacuo to afford a dark oil (28.6 g). Purification by flash chromatography using 2% ethyl acetate in hexanes as solvent provided the title compound (24.7 g, 93%) as a pale yellow oil. MS [(+)ESI, m/z]: 241 [M+H]+ HRMS [(+)ESI, m/z]: 241.12205 [M+H]+. Calcd for C16H17O2: 241.12286 Anal. Calcd for C16H16O2: C, 79.97; H, 6.71. Found: C, 79.67; H, 6.61.

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2006/199806; (2006); A1;,
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140-11-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 140-11-4, name is Benzyl acetate, A new synthetic method of this compound is introduced below.

Into a column (Omnifit (registered trademark), inner diameter: 10 mm), 1.55 g (about 2.4 mL) of an anion exchange resin (DOWEX (registered trademark) 1¡Á2 100-200 Mesh, Cl form) was packed, and the column was placed in a column oven whose temperature was adjusted to 60 C., stood vertically and fixed. Next, 60 mL of 1 mol/L sodium methoxide solution previously prepared was fed into the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump (manufactured by YMC CO., LTD.). Next, 60 mL of methanol was fed into the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump to wash the resin. Subsequently, 34 g of methanol was added to 6 g of benzyl acetate to prepare a homogeneous solution, the prepared solution was passed through the column at a rate of 1.0 mL/min (SV: 25 hr-1) using a syringe pump, and the reaction solution was collected from an outlet of the column. As a result, the reaction solution containing 4.28 g of desired benzyl alcohol was obtained (yield: 99%). It was possible to selectively remove methyl acetate produced as a by-product by concentration operation. In the obtained reaction solution, only methyl acetate was identified, and no acetic acid was identified. Although the reaction rate gradually decreased due to a long-time feeding, the resin was regenerated by feeding a sodium methoxide solution to the column after use, whereby the reaction rate was recovered to the initial reaction rate.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; KANEKA CORPORATION; MACHIDA, Koji; Yasukouchi, Hiroaki; Nishiyama, Akira; US2019/300465; (2019); A1;,
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A common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 25597-16-4.

Step 2: ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (2.5 g, 7.5 mmol) from step 1, triethylamine (2 mL) and ethyl 4,4,4-trifluorocrotonate (5.1 g, 30 mmol) were mixed in DMF (10 mL), and then the system was heated to 85 C. for reaction for 48 hrs. At the end of reaction, the reaction system was cooled to room temperature, added with water and extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.5 g of the product (69%) by column chromatography. 1HNMR (400 MHz, d-CDCl3), delta 7.60 (s, 2H), 7.10 (s, 1H), 5.81 (m, 1H), 4.30 (dd, 2H), 1.33 (m, 3H) MS (MM-ES+APCI), m/z: 481 (M-H+)

The synthetic route of Ethyl 4,4,4-trifluorocrotonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
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110661-91-1, These common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: Preparation of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate A flask was charged with 2-hydroxy-4-(trifluoromethyl)benzaldehyde (300 mg, 1.58 mmol, 1.00 equiv), DMF (10 mL), potassium carbonate (654 mg, 4.73 mmol, 3.00 equiv), and tert-butyl 4-bromobutanoate (702 mg, 3.15 mmol, 2.00 equiv). The resulting solution was stirred overnight at 100 C. and quenched with water (30 mL). The resulting solution was extracted with DCM (2*50 mL) and the organic layers were combined, washed with brine (2*30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was chromatographed on a silica gel column with EtOAc/petroleum ether (1/10) to provide 450 mg (86% yield) of tert-butyl 4-(2-formyl-5-(trifluoromethyl)phenoxy)butanoate as a light yellow solid. 1H NMR (300 MHz, Chloroform-d) delta 10.5 (s, 1H), 7.96 (d, J=7.5 Hz, 1H), 7.29-7.33 (m, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.50 (t, J=6.0 Hz, 2H), 2.18-2.25 (m, 2H), 1.49 (s, 9H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 110661-91-1.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; BUZARD, Daniel J.; SHAGHAFI, Michael B.; (108 pag.)US2018/134674; (2018); A1;,
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6065-82-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6065-82-3 as follows.

TMSOTf (55.2 muL, 305 mumol) was added to a suspension of 23 (31.8 mg, 50.8 mumol) and ethyl diethoxyacetate (27.3 muL, 152 mumol) in dichloroethane (2 mL), and the reaction mixture was heated at 100 C for 21.5 h. As a large amount of starting material still remained at this stage, TMSOTf (18.2 muL, 102 mumol) and ethyl diethoxyacetate (9.1 muL, 50.8 mumol) were added to the reaction mixture and the whole was heated at 100 C for 20.5 h. The reaction mixture was diluted with saturated NaHCO3 (10 mL) and extracted with chloroform (3¡Á30 mL). The combined extracts were washed with brine (30 mL), dried, and concentrated in vacuo to give a residue (60 mg). Chromatography of this residue on a silica gel (10 g) column with chloroform-methanol (100/1) gave 26a (16.1 mg, 46%) as a pale yellow oil. IR (KBr) 3375, 2927, 2854, 1734, 1645, 1460, 1178, 1058 cm-1; 1H NMR (CDCl3, 500 MHz) delta 1.289 (3H, t, J=7.2 Hz, OCH2CH3), 1.86 (3H, s, 12-CH3), 2.11 (3H, s, 3-CH3), 2.26 (1H, dd, J=17.1, 10.7 Hz, 14-Hbeta), 2.50 (3H, s, TsCH3), 2.55 (3H, s, NCH3), 2.78 (1H, d, J=17.4 Hz, 5-Hbeta), 2.97 (1H, dd, J=17.4, 7.6 Hz, 5-Halpha), 3.26 (1H, dd, J=17.1, 4.2 Hz, 14-Halpha), 3.69 (3H, s, 2-OCH3), 3.74 (3H, s, 11-OCH3), 3.83 (3H, s, 10-OCH3), 3.87 (3H, s, 1-OCH3), 3.86-3.90 (1H, overlapped, 6-H), 4.23 (2H, q, J=7.0 Hz, OCH2CH3), 4.24-4.29 (1H, m, 14a-H), 4.31 (1H, br s, 15-H), 4.70 (1H, br s, OH), 6.34 (1H, s, 9-H), 7.38 (2H, d, J=8.2 Hz, 2¡Á2′-H), 7.86 (2H, d, J=8.2 Hz, 2¡Á3′-H); 13C NMR (CDCl3, 125 Hz) delta 8.7 (3-CH3), 10.8 (12-CH3), 14.2 (OCH2CH3), 21.4 (TsCH3), 23.6 (C5), 26.5 (C14), 40.4 (NCH3), 51.2 (C9), 52.4 (C14a), 54.2 (C15), 58.6 (C6), 59.9 (10-OCH3), 60.0 (2-OCH3), 60.3 (1-OCH3), 60.6 (11-OCH3), 61.7 (OCH2CH3), 114.3 (C4a), 117.3 (C3), 122.4 (C9a), 123.0 (C15a), 125.0 (C13a), 127.1 (C12), 128.6 (2¡ÁCH), 129.7 (2¡ÁCH), 133.6 (C1′), 141.0 (C13), 144.7 (C1), 145.3 (C4′), 147.8 (C4), 148.9 (C10), 149.3 (C2), 149.6 (C11), 169.8 (C7), 171.4 (C16); FABMS m/z 711 [M+1]+; HRFABMS m/z 711.2585 (M++1, calcd for C36H43N2O11S, 711.2588).

According to the analysis of related databases, Ethyl diethoxyacetate, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yokoya, Masashi; Shinada-Fujino, Kimiko; Yoshida, Saiko; Mimura, Masahiro; Takada, Hiroki; Saito, Naoki; Tetrahedron; vol. 68; 22; (2012); p. 4166 – 4181;,
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42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a round bottom flask was charged with S11 (10.0 g, 0.056 mol, 1.0 equiv.), tert-butyl methylmalonate (12.3 ml, 0.074 mol, 1.3 equiv.), (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidi-ne (3.7 g, 0.011 mol, 0.2 equiv.), and 100 mL of EtOH. The reaction mixture was stirred atroom temperature for 16 h and was then concentrated in vacuo. Purification of the crudeproduct by flash chromatography on silica gel (petroleum ether:EtOAc, 5:1 v/v) afforded S2as a pair of diastereoisomers (15.1 g, 76percent), both as yellow oil.S2-upper: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.30; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.81 (d,J = 8.8 Hz, 1H), 7.55 (t, J = 7.2 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.39 (t, J = 8.4 Hz, 1H), 4.56 ? 4.50 (m, 1H),3.83 (d, J = 9.2 Hz, 1H), 3.57 (s, 3H), 3.12 ? 2.97 (m, 2H), 1.43 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 199.6,167.9, 166.5, 150.3, 134.8, 132.8, 129.3, 128.2, 124.7, 83.2, 57.2, 52.6, 46.6, 33.7, 27.8, 27.8, 27.8; IR (neat): vmax= 1727, 1355, 845, 749 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7, 374.1210; found 374.1210; [alpha]D25= +63.4 (c 0.20, MeOH).S2-lower: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.26; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.82 (d,J = 8.4 Hz, 1H), 7.55 (t, J = 8 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.38 (t, J = 7.6 Hz, 1H), 4.53 ? 4.47 (m, 1H), 3.87(d, J = 9.6 Hz, 1H), 3.73 (s, 3H), 3.08 ? 2.94 (m, 2H), 1.20 (s, 9H); 13C NMR (100MHz, CDCl3): delta 199.6, 168.4,165.9, 150.2, 135.0, 132.9, 129.5, 128.2, 124.7, 82.8, 57.1, 52.7, 47.3, 34.1, 27.4, 27.4, 27.4; IR (neat): vmax =1727, 1529, 844, 787 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7 374.1210; found 374.1210; [alpha]D25 =+32.5 (c 0.30, MeOH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl methyl malonate, its application will become more common.

Reference:
Article; Wang, Xiaobei; Xia, Dongliang; Qin, Wenfang; Zhou, Ruijie; Zhou, Xiaohan; Zhou, Qilong; Liu, Wentao; Dai, Xiang; Wang, Huijing; Wang, Shuqing; Tan, Ling; Zhang, Dan; Song, Hao; Liu, Xiao-Yu; Qin, Yong; Chem; vol. 2; 6; (2017); p. 803 – 816;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

183322-16-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 183322-16-9 as follows.

1.6 Synthesis of ethyl 6-nitro-3,4-bis(methoxyethoxy)benzoateThe 0.23 mol ethyl 3,4-bis(methoxyethoxy)benzoate dissolved in 230 ml of acetic acid, maintaining the temperature of the systrem at 0-5C, 60 ml concentrated nitric acid was added. warmed to room temperature for 30 min, and continue reaction for 24h. The reaction mixture was poured into the 1000 ml water, ethyl acetate extraction (5¡Á250 ml), combined with the phase, are respectively using saturated NaHCO 3 solution (3x250mL) and saturated NaCl solution (3x250mL) washing, NaSO 4 drying. Activated carbon decolourizations, revolving off a solvent to obtain oil, yield 96%

According to the analysis of related databases, Ethyl 3,4-bis(2-methoxyethoxy)benzoate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Normal University; Qi, Chuanmin; Wang, Xiao; Li, Shilei; He, Yong; Chen, Yurong; (16 pag.)CN103193722; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common heterocyclic compound, 13671-00-6, name is Methyl 2,6-difluorobenzoate, molecular formula is C8H6F2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 13671-00-6.

Step 3: methyl 2,6-difluoro-3-nitrobenzoateTo a solution of methyl 2,6-difluorobenzoate (68.8 g, 0.4 mol) in con. H2SO4 (300 mL) was added potassium nitroperoxous acid (48.5 g, 0.48 mol) for three times and the resulting reaction mixture was stirred at room temperature for 2 hrs. The mixture was droped into ice-water (500 mL) and filtered. The solid was washed with water and dried to afford the desired product (89 g, 100%).1H NMR (DMSC i): ? 8.49-8.43 (1H, m), 7.56-7.51 (1H, m), 3.95 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,6-difluorobenzoate, its application will become more common.

Reference:
Patent; CENTAURUS BIOPHARMA CO., LTD.; XIAO, Dengming; LI, Jijun; ZHU, Yan; HU, Yuandong; WANG, Huting; WANG, Zhe; WANG, Zanping; WEI, Yongheng; SUN, Yinghui; WU, Qiong; ZHANG, Hui; PENG, Yong; KONG, Fansheng; SUN, Ying; LUO, Hong; HAN, Yongxin; WO2013/71865; (2013); A1;,
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Ester – an overview | ScienceDirect Topics

99548-54-6, Name is Methyl 3-bromo-2-methylbenzoate, 99548-54-6, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Preparation Example 13 Under a nitrogen atmosphere, a mixture of methyl 3-bromo-2-methylbenzoate (53.00 g), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (88.10 g), bistriphenylphosphine palladium chloride (8.12 g), triphenylphosphine (6.07 g), potassium acetate (68.10 g), and dioxane (530 mL) was heated and stirred at 100 C. for 29 hours, and then cooled to room temperature. The reaction mixture was filtered through Celite and washed with ethyl acetate. The resulting filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (54.00 g) as a colorless oil.

Statistics shows that Methyl 3-bromo-2-methylbenzoate is playing an increasingly important role. we look forward to future research findings about 99548-54-6.

Reference:
Patent; Negoro, Kenji; Ohnuki, Kei; Yonetoku, Yasuhiro; Kuramoto, Kazuyuki; Urano, Yasuharu; Watanabe, Hideyuki; US2012/35196; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6962-92-1, name is 4-Chlorobutyl acetate, A new synthetic method of this compound is introduced below., 6962-92-1

To a suspension of sodium ethoxide (4 g, 59.18 mmol) in EtOM (50 mL) was added thiophenol (5 g, 45.45 mrnol) at0C, followed by drop-wise addition of 4-chiorobutyl acetate (7 g, 45.45 minol) over a period of 20 mm. and stirred the same temperature for 10 mm. and heated at reflux for 6 h. The RM was cooled the reaction to RT, added KOH pellets (2.6 g, 45.45 inmol), heated at reflux for4 h. After completion, the RM was poured into ice water, extracted with EtOAc (2 times), EtOAc layer was washed with water, brine, dried over anhydrous Na2SO4, filtered and the solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel(60-120 mesh) column chromatography, eluted with 8%EtOAc/pet ether to afford 4-(phenylthio)butan-1-ol as oily mass (6 g, 72%); ?H NMR (400 MHz, cdcl3) 5 7.33 (dd, J = 8.2,1.6 Hz, 2H), 7.30 – 7.23 (m, 2H), 7.20 – 7.14 (m, 1H), 3.65 (td, J = 5.0, 4.1, 3.0 Hz, 2H), 2.96 (t, J = 6.9 Hz, 2H),1.78 – 1.65 (m, 4H); Mass (M+H): 183, LCMS Purity: 99.83%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; NAKASHIMA, Yosuke; JIN, Yoshinobu; WO2014/84407; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics