Tag: M.W=100-200

Application of 27829-72-7, These common heterocyclic compound, 27829-72-7, name is Ethyl E-hex-2-enoate, 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.

To ester 6 (1.97 g, 14.86 mmol) in 9:1H2O/MeOH (100 mL), NaHSO3 (40percent w/v aqueous solution, 4.33 mL,16.64 mmol) and Et3N (2.31 mL, 16.64 mmol) were added. The resultingmixture was heated at reflux for 18 h. The solvent was removed in vacuo, andthe crude product was purified using flash chromatography (10:90:1 to20:80:1, MeOH/CH2Cl2/AcOH) to give acid 7 in 31percent yield as a yellow gum. dH(400 MHz; D2O): 0.94 (3H, t, J = 7.4 Hz, 6-CH3), 1.30 (18H, t, J = 7.3 Hz,(N(CH2CH3)3)2) 1.39?1.61 (3H, m, 5-CH2, 4-Ha), 1.83?1.92 (1H, m, 4-Hb), 2.56(1H, dd, J = 6.9, 16.1 Hz, 2-Ha), 2.81 (1H, dd, J = 6.4, 16.1 Hz, 2-Hb), 3.22 (12H, q,J = 7.5 Hz, (N(CH2CH3)3)2), 3.26?3.33 (1H, m, 3-H); dC (100 MHz; D2O) 8.8((N(CH2CH3)3)2), 13.8 (C-6), 20.2 (C-5), 32.7 (C-4), 36.7 (C-2), 47.3((N(CH2CH3)3)2), 57.6 (C-3), 178.2 (C-1); IR: mmax cm1 2987, 2704, 1716,1565, 1389, 1228, 1148; HRMS (ESI) found [MH2(Et3N)]+ 195.0333,C6H11O5S, required 195.0332. In a second fraction was obtained ester 8 (1.20 g,25percent) as a yellow oil. 1H (400 MHz; D2O): 0.95 (3H, t, J = 7.3 Hz, 6-CH3), 1.28?1.32 (12H, m, OCH2CH3, N(CH2CH3)3), 1.38?1.46 (1H, m, 4-Ha), 1.48?1.59 (2H,m, 5-CH2), 1.88?1.89 (1H, m, 4-Hb), 2.65?2.81 (2H, m, 2-CH2), 3.23 (6H, q,J = 7.2 Hz, N(CH2CH3)3), 3.31?3.36 (1H, m, 3-H), 4.20 (2H, q, J = 7.2 Hz,OCH2CH3); 13C (100 MHz; D2O): 8.2 (N(CH2CH3)3), 13.1 (C-6 and OCH2CH3),19.5 (C-5), 31.8 (C-4), 35.4 (C-2), 46.7 (N(CH2CH3)3), 56.8 (C-3), 62.1(OCH2CH3), 177.0 (C-1); IR: mmax cm1 2964, 2708, 1723, 1468, 1375, 1224;HRMS (ESI). Found [MHEt3N]+ 223.0652, C8H15O5S, required 223.0646.

Statistics shows that Ethyl E-hex-2-enoate is playing an increasingly important role. we look forward to future research findings about 27829-72-7.

Reference:
Article; Duhamel, Nina; Piano, Federico; Davidson, Samuel J.; Larcher, Roberto; Fedrizzi, Bruno; Barker, David; Tetrahedron Letters; vol. 56; 13; (2015); p. 1728 – 1731;,
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Application of 217314-47-1, These common heterocyclic compound, 217314-47-1, name is Methyl 3-amino-5-methoxybenzoate, 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.

Aniline 14.4 is treated which sulfonyl chloride 2 to give the corresponding sulfonamide 15.2, which is followed by the treatment of NaH to afford the cyclic sulfonamide 15.3. Basic hydrolysis (LiOH, H20/THF/MeOH) of compound 15.3 gives acid 15.1 as the intermediateds for example 57.

The synthetic route of 217314-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNESIS PHARMACEUTICALS, INC.; WO2003/106405; (2003); A1;,
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Related Products of 4341-76-8, 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. 4341-76-8, name is Ethyl 2-butynoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a two neck rbf was stirred a mixture of Pd(OAc)2 (275 mg,1.22 mmol) and TDMPP (540 mg, 1.22 mmol) in benzene (30 ml)for 15 min at rt under nitrogen. To this mixture was added ethyl-2-butynoate 7 (2.84 ml, 24.48 mmol) and the resulting mixturewas further stirred for 10 min at rt. Next, ethynylbenzene 4a(2.50 g, 24.48 mmol) was added to this solution and the mixturewas stirred for 5-10 min until reaction was completed. Theworkup of reaction was performed by evaporating the solvent invacuum followed by column chromatography (Hexane:EtOAc = 100:1) to give the desired compound 8a (2.62 g);

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

Reference:
Article; Singh, Sarbjit; Goo, Ja-Il; Noh, Hyojin; Lee, Sung Jae; Kim, Myoung Woo; Park, Hyejun; Jalani, Hitesh B.; Lee, Kyeong; Kim, Chunsook; Kim, Won-Ki; Ju, Chung; Choi, Yongseok; Bioorganic and Medicinal Chemistry; vol. 25; 4; (2017); p. 1394 – 1405;,
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Application of 6290-49-9, These common heterocyclic compound, 6290-49-9, name is Methyl 2-methoxyacetate, 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.

A mixture of methyl methoxyacetate (52 g, 500 mmol), hydrazine hydrate (30 mL) washeated to reflux for 8 h. Excess hydrazine and water were removed under vacuum. The residuewas extracted with n-butanol, dried with NaaSC^. Excess w-butanol was removed to yield 45g ofhydrazide.

The synthetic route of 6290-49-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS; WO2004/108661; (2004); A1;,
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Electric Literature of 13195-64-7,Some common heterocyclic compound, 13195-64-7, name is Diisopropyl malonate, molecular formula is C9H16O4, 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.

In 820mmol of sodium hydride as catalyst, 200mmol 440mmol diisopropyl malonate with propargyl bromide was added to 250mLof anhydrous acetonitrile in an ice-water bath with stirring for 8 hours, the product was washed with water, added with ethyl acetate, spin dried under reduced pressure, ethyl acetate: petroleumether = 1: 100 (volume ratio) as eluent column chromatography, the desired product was collected and concentrated to give a white solid product, i.e. compound a-1;

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui Normal University; Lu, Shuang; Hu, Yimin; (14 pag.)CN105777679; (2016); A;,
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Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. category: esters-buliding-blocks

To a solution of CuI (1.8 g, 9.6 mmol) and TMEDA (3.6 mL, 24 mmol) in THF (1.0 mL) was added 2-phenylethylmagnesium bromide (0.7 M in THF, 13.7 mL, 9.6 mmol) at -40 C, and the resulting mixture was stirred at -40 C for 30 min. To the mixture was added ethyl 2-butynoate (0.9 g, 8 mmol) at -78 C, and the mixture was stirred at -78 C for 2 h. Saturated NH4Cl aq was added and the mixture was allowed to warm to rt. The resulting slurry was diluted with EtOAc (50 mL) and washed with H2O and brine. The organic layer was separated and dried over MgSO4. Then, the drying agent was removed by filtration, and the resulting solution was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-10% EtOAc/hexane) provided ethyl (E)-3-methyl-5-phenyl-2-pentenoate (1.7 g, 7.6 mmol) in 95% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.

Reference:
Article; Hojoh, Kentaro; Shido, Yoshinori; Nagao, Kazunori; Mori, Seiji; Ohmiya, Hirohisa; Sawamura, Masaya; Tetrahedron; vol. 71; 37; (2015); p. 6519 – 6533;,
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Electric Literature of 3618-04-0,Some common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, molecular formula is C9H16O3, 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 1 : To a stirred solution ethyl 4-hydroxycyclohexanecarboxylate (2.78 g, 16.0 mmol, 1 equiv.) in dry THF (80 mL), was added dropwise lithium aluminum hydride (1 M in THF, 24 mL, 24.0 mmol, 1 .5 equiv.) at 0¡ãC under azote atmosphere. The reaction mixture was warmed to room temperature and stirred for 3h30. The mixture was then cooled to 0¡ãC and water (1 ml_), 15percent aqueous sodium hydroxide (1 mL) and water (3 mL) were successively added. The mixture was allowed to warm to room temperature and stirred overnight. The salts were filtered through a pad of celite and the filtrate was dried over Na2S04 and concentrated under vacuum to yield 4- (hydroxymethyl)cyclohexanol (2.10 g, quant.) as a colorless oil.

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BCI PHARMA; SURLERAUX, Dominique; AMIABLE, Claire; GUILLON, Remi; (239 pag.)WO2017/191297; (2017); A1;,
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These common heterocyclic compound, 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, 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. HPLC of Formula: C8H5F3O2

To a solution of 5-chloro-[1,1?-biphenyl]-2-ol (5.0 g, 24.4 mmol) in anhydrous dimethyl sulfoxide (50 mL) was added potassium carbonate (5.1 g, 36.6 mmol) and methyl 2,4,5-trifluorobenzoate (4.4 g, 24.4 mmol) and the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was partitioned between ethyl acetate (400 mL) and water (100 mL), and the organic phase washed with water (50 mL x 2), brine (50 mL); dried over anhydrous sodium sulfateand concentrated in vacuo to yield the title compound as a colorless foam (8.9 g, quant. yield): ?HNMR (300 MHz, CDC13) oe 7.61 (dd, J = 10.9, 6.6 Hz, 1H), 7.48-7.42 (m, 3H), 7.37-7.26 (m, 4H), 7.05 (d, J = 8.6 Hz, 1H), 6.39 (dd, J = 11.1, 6.6 Hz, 1H), 3.85 (s, 3H).

The synthetic route of Methyl 2,4,5-trifluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; XENON PHARMACEUTICALS INC.; ANDREZ, Jean-Christophe; BERGERON, Philippe; BICHLER, Paul, Robert; CHOWDHURY, Sultan; DEHNHARDT, Christoph, Martin; FOCKEN, Thilo; GONG, Wei; GRIMWOOD, Michael, Edward; HASAN, Abid; HEMEON, Ivan, William; JIA, Qi; SAFINA, Brian; SUN, Shaoyi; WILSON, Michael, Scott; ZENOVA, Alla, Yurevna; (436 pag.)WO2016/7534; (2016); 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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., Computed Properties of C7H11ClO4

DBU (4.64 g, 30.5 mmol) was added at room temperature to a solution of 8 (7.00 g, 27.7 mmol) and diethyl chloromalonate (6.47 g, 33.2 mmol) in DMF (70 ml). After stirring at this temperature for 24 h, the reaction mixture was quenched with H2O (200 ml) at 0 ¡ãC. The aqueous layer was extracted with AcOEt (200 ml ¡Á 2). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane-AcOEt) to give 9 (4.67 g, 50percent) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta 1.38 (3H, t, J = 7.1 Hz), 1.47 (9H, s), 1.87-1.95 (2H, m), 2.38-2.49 (1H, m), 2.74-2.87 (2H, m), 4.10-4.28 (2H, m), 4.35 (2H, q, J = 7.1 Hz), 4.50 (2H, br s), 7.06 (1H, s).

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:
Article; Koshizawa, Tomoaki; Morimoto, Toshiharu; Watanabe, Gen; Watanabe, Toshiaki; Yamasaki, Nao; Sawada, Yoshikazu; Fukuda, Tomoaki; Okuda, Ayumu; Shibuya, Kimiyuki; Ohgiya, Tadaaki; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3249 – 3253;,
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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 13671-00-6 as follows. Safety of Methyl 2,6-difluorobenzoate

Example 43A 2,6-Difluorophenyl)(2H2)methanol At 0 C., 1.00 g (5.81 mmol) of methyl 2,6-difluorobenzoate were initially charged in 20 ml of THF, and 11.62 ml of (11.62 mmol) of lithium aluminium deuteride [=LiAlD4=lithium tetrahydrido(2H4)aluminate](1 M solution in THF) were added dropwise. The mixture was stirred for 1 h in an ice bath that slowly thawed. 0.58 ml of water, 0.58 ml of 2 N aqueous sodium hydroxide solution and 1.16 ml of water were then added in succession to the reaction solution. The precipitate formed was filtered off and washed thoroughly with THF. The filtrate was concentrated and the residue was dried under high vacuum. This gave 0.743 g of the product (88% of theory, purity about 90%), which was reacted further without purification. LC-MS (Method 14): Rt=2.38 min MS (EIpos): m/z=146 (M)+ 1H NMR (400 MHz, DMSO-d6): delta=5.20 (s, 1H), 7.08 (t, 2H), 7.39 (quint, 1H).

According to the analysis of related databases, 13671-00-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; HARTUNG, Ingo; FOLLMANN, Markus; JAUTELAT, Rolf; STRAUB, Alexander; HAssFELD, Jorma; LINDNER, Niels; SCHNEIDER, Dirk; WUNDER, Frank; STASCH, Johannes-Peter; REDLICH, Gorden; LI, Volkhart Min-Jian; BECKER-PELSTER, Eva Maria; KNORR, Andreas; US2014/128386; (2014); A1;,
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