Category: 15963-40-3

Synthetic Route of 15963-40-3, 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. 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry three-neck flask was charged with methyl 3-methylenecyclobutanecarboxylate (6 g, 47.6 mmol) and dry THF (20 ml) and cooled to -10 C. BH3.THF (12.26 g, 143 mmol) was then added via a syringe dropwise. The resulting mixture was stirred for 4h at rt and was cooled to -20 C – 10C. Methanol was then added and the mixture was stirred for 15min. Sodium hydroxide (3M; 30 ml) and H2O2 (7.29 ml_, 238 mmol) were added in sequence. The mixture was stirred for 2h and a saturated sodium sulfite solution (100 ml) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and the residue was purified by flash chromatography eluting with (petroleum ether/EtOAc = 3/1 ) to afford methyl 3- (hydroxymethyl)cyclobutanecarboxylate (250 mg, 1 .387 mmol, 2.92 % yield) as a yellow oil.

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, Methyl 3-methylenecyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, 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 15963-40-3, Application In Synthesis of Methyl 3-methylenecyclobutanecarboxylate

To a methyl acetate (45 mL) solution of methyl 3-methylenecyclobutanecarboxylate (Intermediate 43A) was added copper powder (2.77 g, 43.6 mmol) and zinc powder (5.70 g, 87 mmol). To this mixture was added a methyl acetate (45 mL) solution of 2,2,2-trichloroacetyl chloride (4.86 mL, 43.6 mmol) and phosphorus oxychloride (0.37 mL, 4.0 mmol) dropwise over 2 h. After 3 h, the reaction was cooled to 0 C, and additional zinc powder (5.70 g, 87 mmol) was added, followed by acetic acid (22.7 mL, 400 mmol) dropwise at a rate keeping the temperature below 7 C. The reaction was allowed to slowly warm to room temperature and after stirring overnight was filtered through Celite, rinsing with EtOAc. The filtrate was carefully washed (warning: gas evolution) with saturated aqueous NaHC03 (2 X 200 mL), and the aqueous layers extracted with 1 :1 EtOAc:Et20 (2 X 100 mL). The combined organic layers were dried over MgS04, filtered and concentrated, and the residue purified on silica gel eluting with a 0%-50% EtOAc-hexanes gradient. The appropriate fractions were combined, evaporated under reduced pressure and placed in vacuo to give the title compound (4.10 g, 61 %) as a yellow oil. 1H NMR (400 MHz, CDCI3) delta 2.38-2.48 (m, 2 H), 2.50-2.61 (m, 2 H), 3.00- 3.09 (m, 2 H), 3.09-3.22 (m, 3 H), 3.68 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-methylenecyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 15963-40-3, These common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, 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.

3.1.57b (24 g, 190.4 mmol, 1.0 equiv) was dissolved in THE and cooled to -15 C. BH3.Me2S (14.4 g, 190.4 mmol, 1.0 equiv) was added drop wise and the reaction mixture was stirred at room temperature for 4 hours. Cooled the reaction mixture at -15 C, NaOH (3M) (25 mL), H202 (50%) (12.9 g, 190.4 mmol, 1.0 equiv) were added and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sodium bisulphate and extracted with EtOAc. The organic layer was washed with brine,dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (70 % EtOAc in Hexane) to afford product 3.1.57c (18.7 g, 68 % yield). 1H NMR (400 MHz, DMSO) 64.54 (d, J = 29.8 Hz, 1H), 3.62-3.55 (m, 3H), 3.41 (d, J = 6.5 Hz, 1H), 3.30 (d, J = 6.0 Hz, 1H), 3.13-2.95 (m, 1H), 2.37-2.27 (m, 1H), 2.15 (ddt, J= 8.7, 7.8, 6.2 Hz, 2H), 1.98- 1.84(m, 2H).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FU, Jiping; LEE, Patrick; MADERA, Ann Marie; SWEENEY, Zachary Kevin; WO2015/66413; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 15963-40-3,Some common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, molecular formula is C7H10O2, 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 borane-THF (56 mL, 0.80 eq.) was added dropwise over 30 mm to a cold (-10 C) solution of methyl 3-methylidenecyclobutane-1-carboxylate (10 g, 79.27 mmol, 1.00 eq.) in THF (100 mL). The resulting solution was stirred for 3 hours at 25 C. The mixture was cooled to -10 Cand methanol (20 mL) was added slowly and the mixture was stirred for 30 mm at 25 C. The reaction mixture was cooled to -10 C and H202 (9 g, 79.41 mmol, 1.00 eq., 30%) was added dropwise (5 mm) followed by dropwise addition of sodium hydroxide aqueous (12.5 mL) at -10C. The resulting solution was stirred for 3 hours at 25 C. The reaction was then quenched by the addition of Na2SO3 aqueous. The resulting solution was diluted with water (300 mL) andthen extracted with ethyl acetate (2×300 mL) and the organic layers combined. The resulting mixture was washed with brine (2×300 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give methyl 3 -(hydroxymethyl)cyclobutane- 1 -carboxylate as colorless oil (6.6 g, 58%).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 15963-40-3, 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. 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry three-neck flask was charged with methyl 3-methylenecyclobutanecarboxylate (6 g, 47.6 mmol) and dry THF (20 ml) and cooled to -10 C. BH3.THF (12.26 g, 143 mmol) was then added via a syringe dropwise. The resulting mixture was stirred for 4h at rt and was cooled to -20 C – 10C. Methanol was then added and the mixture was stirred for 15min. Sodium hydroxide (3M; 30 ml) and H2O2 (7.29 ml_, 238 mmol) were added in sequence. The mixture was stirred for 2h and a saturated sodium sulfite solution (100 ml) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and the residue was purified by flash chromatography eluting with (petroleum ether/EtOAc = 3/1 ) to afford methyl 3- (hydroxymethyl)cyclobutanecarboxylate (250 mg, 1 .387 mmol, 2.92 % yield) as a yellow oil.

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, Methyl 3-methylenecyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 15963-40-3, The chemical industry reduces the impact on the environment during synthesis 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, I believe this compound will play a more active role in future production and life.

To a solution of Et2Zn (11.89 mL, 11.89 mmol) in DCM (10 mL) was added a solution of TFA (0.88 mL, 11.89 mmol) in DCM (10 mL) dropwise at 0 C for 30 minutes. A solution of CH2I2 (0.96 mL, 11.89 mmol) in DCM (10 mL) was added dropwise at 0 C for 45 minutes. The reaction mixture was stirred at 0 C for 1 hour. A solution of methyl 3- methylenecyclobutanecarboxylate (500 mg, 3.96 mmol) in DCM (5 mL) was added to the reaction mixture. The reaction mixture was allowed to warm to 15 C for 16 hours. Saturated NH4CI solution (50 mL) was added to the reaction mixture and the mixture was extracted with DCM (50 mL c 2). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated. The crude residue was purified by silica gel column chromatography (10 % EtOAc in petroleum ether) to afford the title compound (400 mg, 72 %) as a yellow oil. ‘ H NMR (400 MHz, CDCl3) d 3.71 (s, 3H), 3.34 – 3.27 (m, 1H), 2.53 – 2.48 (m, 2H), 2.26 – 2.20 (m, 2H), 0.49 – 0.42 (m, 4H).

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, Methyl 3-methylenecyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; CUNNINGHAM, Christian; BEROZA, Paul Powell; CRAWFORD, James John; LEE, Wendy; RENE, Olivier; ZBIEG, Jason Robert; LIAO, Jiangpeng; WANG, Tao; YU, Chen; (208 pag.)WO2020/51099; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 15963-40-3,Some common heterocyclic compound, 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate, molecular formula is C7H10O2, 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 solution of methyl 3-methylenecyclobutanecarboxylate (5.3 g, 42.4 mmol, 1.0 eq) in THF (30 mL) was added BH3 (12.6 mL, 12.6 mmol, 0.3 eq, 1 M) dropwise at 0 C. Then the reaction mixture was warmed to ft and stirred for 4 h. MeOH (15 mL) was added and the mixture was stirred for 30 mm at 0 C. NaOH (4.2 mL, 3M) and H202 (1.4 g, 42.4 mmol, 1.0 eq) wereadded and stirred at 0 C for 1 h. The mixture was quenched with water (30 mL) and extracted with Et20 (60 mL X 2). The combined organic phases were dried over Na2SO4 After filtration and concentration, 3.3 g of methyl 3-(hydroxymethyl)cyclobutanecarboxylate as yellow oil was obtained. Y: 54%. ESI-MS (M+H): 145.0. ?H NMR (400 MHz, CD3OD) (5: 3.69 (s, 1.3H), 3.67 (s, 1.7H), 3.59 (s, 0.4H), 3.58 (s, 0.5H), 3.50 (s, 0.4H), 3.48 (s, 0.5H), 3.12-3.03 (m, 1H), 2.48-2.38 (m, 1H), 2.35-2.22 (m, 2H), 2.08-1.94 (m, 2H).

The synthetic route of 15963-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN MA INC.; CHAN, Timothy; GUCKIAN, Kevin; JENKINS, Tracy; THOMAS, Jermaine; VESSELS, Jeffery; KUMARAVEL, Gnanasambandam; MEISSNER, Robert; LYSSIKATOS, Joseph, P.; LUCAS, Brian; LEAF, Irina; DUFFIELD, Jeremy; GENUNG, Nathan; (113 pag.)WO2017/127430; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics