Tag: M.W=100-200

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. 1260092-46-3, name is tert-Butyl 3-(2-aminoethoxy)propanoate, A new synthetic method of this compound is introduced below., Application In Synthesis of tert-Butyl 3-(2-aminoethoxy)propanoate

To a solution of fert-butyl 3-(2-aminoethoxy)propanoate (246 mg, 1.302 mmol) in DMF (1.5 ml) at rt was added bis(2,5-dioxopyrrolidin-l-yl) 3,3′-oxydipropanoate (232 mg, 0.651 mmol) and followed DIPEA (0.284 ml, 1.628 mmol). The mixture was allowed to stir at rt over night and concentrated to dryness. To the resulting residure at 0 C was added 1.0 mL neat TFA, and the resulting mixture was allowed to stir at rt overnight. The mixture was concentrated to give the crude product, which was used without further purification. UPLC-MS Method A: TR = 0.7 min, m/z = 393 (z = 1).

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; MERCK SHARP & DOHME CORP.; LIN, Songnian; YAN, Lin; HUO, Pei; PISSARNITSKI, Dmitri; FENG, Danqing; NARGUND, Ravi; MADSEN-DUGGAN, Christina; ZHU, Yuping; KEKEC, Ahmet; WU, Zhicai; (191 pag.)WO2017/205309; (2017); A1;,
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Electric Literature of 153597-59-2,Some common heterocyclic compound, 153597-59-2, name is Ethyl 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2-carboxylate, molecular formula is C9H12N2O3, 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.

N-Bromosuccinimide (6.00 g, 33.7 mmol) was added portion-wise to a solution of C2 (6.00 g, 30.6 mmol) in acetonitrile (100 mL). After the reaction mixture had been stirred at 50 C for 1 hour, it was allowed to cool to room temperature, concentrated in vacuo, and partitioned between ethyl acetate (200 mL) and water (150 mL). The organic layer was washed with water (150 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 20% to 80% ethyl acetate in heptane) provided material that contained residual succinimide; this was dissolved in ethyl acetate (100 mL), washed with water (2 x 100 mL) and with saturated aqueous sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting yellow solid was triturated with pentane to afford the product as a white powder. Yield: 6.00 g, 21.8 mmol, 71 %. LCMS m/z 276.9 (0287) (bromine isotope pattern observed) [M+H]+. 1H NMR (400 MHz, CDCI3) delta 4.44-4.40 (m, 2H), 4.42 (q, J=7.1 Hz, 2H), 4.26 (t, J=6.2 Hz, 2H), 2.36-2.29 (m, 2H), 1 .41 (t, J=7.1 Hz, 3H).

The synthetic route of 153597-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; PATEL, Nandini Chaturbhai; VERHOEST, Patrick Robert; HELAL, Christopher John; SCIABOLA, Simone; LACHAPELLE, Erik Alphie; WAGER, Travis T.; HAYWARD, Matthew Merrill; (127 pag.)WO2017/145013; (2017); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 93-92-5, name is 1-Phenylethyl acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Phenylethyl acetate

General procedure: A 1,2-dichloroethane (5.0mL) solution of isopropenyl acetate (2a) (0.3mmol), 1-phenylethyl acetate (10a) (0.3mmol) and ReBr(CO)5 was stirred under an atmosphere of nitrogen at 80C for 5h. After the reaction was complete, H2O was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried with MgSO4. The resulting mixture was filtered, and the filtrate was concentrated. Purification of the residue by silica gel column chromatography afforded 4-phenyl-2-pentanone (3a). The product (3a) was characterized by comparing its spectral data with those of authentic sample [23].

The synthetic route of 93-92-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Umeda, Rui; Takahashi, Yuuki; Yamamoto, Takaaki; Iseki, Hideki; Osaka, Issey; Nishiyama, Yutaka; Journal of Organometallic Chemistry; vol. 877; (2018); p. 92 – 101;,
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Reference of 1462-12-0, These common heterocyclic compound, 1462-12-0, name is Diethyl 2-ethylidenemalonate, 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.

EXAMPLE 8 3,6-Dimethyl-5-oxoheptanoic acid 8-A. (1,4-Dimethyl-3-oxopentyl)propanedioic acid, diethyl ester A cold (0 C.) solution of 2,2,6,6-tetramethylpiperdine (10.241 gm, 72.5 mmol) in tetrahydrofuran (120 mL) was treated with n-butyl lithium (2.5 M in hexane, 29.0 mL, 72.5 mmol). The light yellow solution was stirred at 0 C. for 30. minutes, then cooled to -78 C. and treated with neat methyl isopropyl ketone (7.70 mL, 6.20 gm, 72 mmol) over a five-minute period. After 50 minutes, a solution of diethyl ethylidenemalonate (10.000 gm, 53.7 mmol) in tetrahydrofuran (7 mL) was added to the above mixture over a 10-minute period. After 50 minutes, the mixture was quenched with glacial acetic acid (5.0 ml) and warmed to room temperature. The mixture was poured into 50% saturated ammonium chloride and extracted with ethyl ether. The ethyl ether extract was washed with 1 N hydrochloric acid, water, and brine, then dried (magnesium sulfate), filtered and stripped to give a pale yellow oil. Distillation of the oil (P=0.15-0.2 mm Hg) afforded compound 8-A (10.883 gm, 74%) as a colorless liquid which boiled at 110-114 C. Thin layer chromatography: Rf =0.25 (20% ethyl acetate in hexane).

The synthetic route of 1462-12-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US5072023; (1991); A;,
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Related Products of 29006-01-7,Some common heterocyclic compound, 29006-01-7, name is Methyl 4-methoxybutanoate, molecular formula is C6H12O3, 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.

Example 1 Preparation of the compound of formula (I) (referred as ACGET61 ) Formula (I) In a round-bottomed flask equipped with an efficient condenser and a magnetic stirrer, Ri (MW: 175.088; 4.43g) and R2 (MW:132.16; 3.347g) are added in an 1 :1 molar ratio. NH4CI (443mg) is then added as catalyst (10% by weight with respect to Ri). The mixture is heated at 150C for 45h and it assumes a deep green / dark purple colour. The disappearance of the reagent is monitored by TLC (AcOEt: Hexane 1 :2) using ninhydrin as detecting agent (prepared dissolving 200mg ninhydrin in 150 ml EtOH). When the reagent is completely disappeared, the reaction mixture is cooled and the residue is dissolved in DCM, washed three times with HCI 3N then with water till neutral pH. The crude product thus obtained is purified by column chromatography eluting with a gradient of AcOEt: Hexane (from 1 : 10 to 1 :1 ). The pure product (ACGET61 , MW 275.1 1 ) is obtained as a white / light pink solid in 64% yield.

The synthetic route of 29006-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIO FARMACEUTICO C.T. S.R.L.; CACCIAGLIA, Roberto; LOCHE, Antonella; (33 pag.)WO2017/21438; (2017); A1;,
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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. 587-47-3, name is Ethyl 2-(3-fluorophenyl)acetate, A new synthetic method of this compound is introduced below., Computed Properties of C10H11FO2

To a solution of ethyl 2-(3-fluorophenyl) acetate (2.0 g, 10.98 mmol) in THF (20 mL), was added potassium bis(trimethylsilyl) amide (1.0 M solution in THF; 12.1 mL, 12.1 mmol), dropwise. The reaction mixture was stirred at rt for 15 mi and then 2-bromo-1,1-diethoxyethane (2.38 g, 12.1 mmol) was added, dropwise. The mixture was heated at 45 C for 1 h, then was cooled to 0 C and was treated with saturated NH4C1 solution (10 mL) and water (50 mL). The mixture was extracted with MTBE (3 x 50 mL). The combined organic phase was washed with water and brine, dried over Na2SO4 and concentrated. This product was taken up in water (7.5 mL) and was treated with a mixtureof chloroform (25 mL) and TFA (25 mL) and was stirred at 0 C to 10 C for 2 h. The reaction mixture was poured into a mixture of 1M solution of K2C03 (125 mL) and dichloromethane (200 mL). Solid K2C03 was added until pH 7.5 was reached. The organic layer was separated, washed with water and brine, dried over Na2504 and concentrated. The crude product was purified by flash chromatography (10% – 15%EtOAc/hexanes gradient) to give Intermediate 1OA (0.95 g, 4.24 mmol, 39% yield).GCMS m/z = 224; NMR (300 MI-Tz, chloroform-d) oe ppm 9.78 (s, 1 H), 7.35 – 7.26 (m, 1H), 7.12 – 6.94 (m, 3 H), 4.23 -4.04 (m, 3 H), 3.40 (dd, J = 9.8, 18.6 Hz, 1 H), 2.83 (dd, J= 4.7, 18.3 Hz, 1 H), 1.23 (t, J = 7.1 Hz, 3H).

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; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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Reference of 1462-12-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1462-12-0, name is Diethyl 2-ethylidenemalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of diethyl ethylidene malonate A (96 g; 0.51 mol), S-methyl isothiourea (71.1 g; 0.79 mol) and triethylamine (80 mL) in 530 mL of abs. ethanol, was refluxed for 3 h under magnetic stirring. The reaction mixture was filtered, and the ethanol concentrated under vacuum, water was added (400 mL) and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and concentrated. The crude reaction mixture was purified by silica gel column chromatography (eluant: n-hexane/ethyl acetate=7/3) to yield compound B (63.7 g; 55%) as a pure solid. 1H-NMR (400 Mhz, DMSO-d6), ppm: 1.16 (d, j=6.6 Hz, 3H); 1.17 (t, j=7.2 Hz, 3H); 3.29 (d, j=10.5 Hz, 1H); 3.84 (dq, j=6.6, 10.5 Hz, 1H); 4.21 (m, 2H);

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl 2-ethylidenemalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia Italia S.p.A.; US2004/9993; (2004); A1;,
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Application of 2967-93-3,Some common heterocyclic compound, 2967-93-3, name is Methyl 2-fluoro-5-methylbenzoate, molecular formula is C9H9FO2, 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.

A solution of methyl 2-fluoro-5-methylbenzoate (6.72 g, 40 mmol)Was added to the reaction flask, CC14 (1 OOmL) was added, NBS (7.47 g, 42 mmol) was added, AlphaIBN (1.29 g, 8 mmol)(100 mL) was added, washed with saturated NaCl (50 mL X3), dried over anhydrous magnesium sulfate, column chromatography (EpsilonAlpha: Rho = 1: 150), and the reaction mixture was heated to reflux. Afforded 6.4 g of white solid in 65% yield.

The synthetic route of 2967-93-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Xu Boling; Chen Xiaoguang; Zhou Jie; Ji Ming; Yao Haiping; Zhou Qin; (57 pag.)CN107098886; (2017); A;,
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Some common heterocyclic compound, 3681-71-8, name is cis-3-Hexenyl acetate, molecular formula is C8H14O2, 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. Application In Synthesis of cis-3-Hexenyl acetate

EXAMPLE 8 Preparation of cis 3-hexen-1-yl 3-(beta-naphthyl)-3-oxo-propionate Lithium diisopropylamide (133.0 mL of a 2.0 M solution, 0.266 mol) is placed into a 500 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78 C. cis 3-Hexenyl acetate (17.80 g, 0.125 mol) is dissolved in THF (10 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of 2-naphthoyl chloride (22.51 g, 0.118 mol) dissolved in THF (30 mL) over 30 min. The mixture is warmed to -20 C. and stirred at that temperature for 18 h. After warming to 0 C., the mixture is quenched with 20% HCl (70 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2*100 mL), water (2*150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an orange/red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1 H and 13 C NMR spectra consistent with the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3681-71-8, its application will become more common.

Reference:
Patent; The Procter & Gamble Company; US6100233; (2000); A;,
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Adding a certain compound to certain chemical reactions, such as: 1462-12-0, name is Diethyl 2-ethylidenemalonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1462-12-0, Formula: C9H14O4

General procedure: In the following examples, if, Ig, Ih, and Ii are radical precursors, respectively, and reacted with Michael acceptor II to obtain an addition product III.Using the optimal reaction conditions:Base K2HPO4, photocatalyst [Ir(ppy)2(dtbbpy)]PF6 (1 mol%), solvent acetone (concentration: 0.2 M), light source 34W blue LED bulb, reaction temperature 40 C.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diethyl 2-ethylidenemalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan University; Song Hao; Qin Yong; Xue Fei; Liu Xiaoyu; Zhang Dan; Wang Falu; Liu Jiazhen; Di Jiamei; Liao Qi; Lu Huifang; Zhu Min; He Liping; (29 pag.)CN108456156; (2018); A;,
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