Category: 3618-04-0

Related Products 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.

tert-Butyldimethylsilyl chloride (26.3 g, hydroxycyclohexanecarboxylate (25.0 g, 171 59-80-7) and imidazole (24.7 g, 363174 mmol) was added to a solution of ethyl 4-145 mmol, mixture of cis-/trans-isomers, Gas Nommol) in N,N-dimethylformamide (36 ml) and the mixture was stirred over night at room temperature. For work-up, water was added and the mixture was extracted with tert-butyl methyl ether (3x). The combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressure to yield ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexanecarboxylate (43.1 g, 104% yield) which was used in the next step without further purification. 1HNMR (400 MHz, DMSO-d6, mixture of isomers): 6 [ppm] = 4.10-3.99 (m, 2H), 3.93-3.86 (m, 0.7H), 3.63-3.51 (m, 0.3H), 2.39-2.28 (m, 0.8H), 2.27-2.14 (m, 0.3H), 1.91-1.21 (m, 8H), 1.20-1.13 (m, 3H), 0.89-0.79 (m, 9H), 0.08-0.00 (m, 6H).

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); A1;,
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Synthetic Route 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.

EXAMPLE B Ethyl 4-oxocyclohexanecarboxylate Ethyl 4-hydroxybenzoate is reduced to ethyl 4-hydroxycyclohexanecarboxylate according to the procedure described in R. A. Finnegan and P. L. Bachman, Journal of Organic Chemistry, Volume 30, pages 4145-4150 (1965). The crude material obtained in this reduction (190 g) is dissolved in 1200 ml of reagent grade acetone. The solution is cooled to 0 C. and 152 ml of a 8 N chromic acid solution (prepared from concentrated sulfuric acid and chromium trioxide) is added dropwise to the mechanically stirred reaction mixture. Enough isopropanol is added to the mixture to discharge its red color and it is then filtered through Celite. The salts are washed with several portions of acetone. The filtrate is evaporated in vacuo. The residue is dissolved in 750 ml of diethyl ether and washed with sodium bicarbonate and brine solutions. After drying, the solvent is evaporated and the residue is distilled to yield the title compound; bp12 125 C. In a process analogous to Example B using appropriate starting materials the following compound is prepared:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route trans-Ethyl 4-hydroxycyclohexanecarboxylate, its application will become more common.

Reference:
Patent; Warner-Lambert Company; US4988699; (1991); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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 Ethyl 4-oxocyclohexanecarboxylate (33.0) STR44 To a 3-L 3-neck flask equipped with a mechanical stirrer, a thermometer, and an addition funnel were added 50 g (292 mmol) of the compound of Formula 32.0 from Step 1, 33 mL (584 mmol) of acetic acid and 145 mL of commercial bleach (5.25percent NaOCl). To the cooled reaction mixture, at 5¡ã C., was added dropwise 479 mL of more bleach. The reaction was allowed to warm to room temperature for 1 hour and then was extracted with 3*400 mL ethyl acetate. The combined extract was washed with water, dried over MgSO4, and concentrated to give 49 g of crude 33.0 as an oil which was used without purification. The spectrum data are identical to that of literature (see Sanchez, I. H.; Ortega, A.; Garcia, G.; Larraza, M. I.; Flores, H. J. Synthetic comm. 1985, 15, 141).

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

Reference:
Patent; Schering Corporation; US5648484; (1997); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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 3618-04-0, Quality Control of trans-Ethyl 4-hydroxycyclohexanecarboxylate

To a solution of ethyl 4-hydroxycyclohexanecarboxylate (5.00 g, 29.0 mmol) in dichloromethane (30 mL) was added 3,4-dihydro-2H-pyran (2.52 g, 29.0 mmol) and Amberlyst 15 (0.5 g). The reaction mixture was stirred at room temperature for 72 h, then another prtion 3,4-dihydro-2H-pyran (1.89 g, 21.8 mmol) and Amberlyst 15 (0.5 g) was added, then after 5 h the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound as a yellow oil (9 g), which was used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, trans-Ethyl 4-hydroxycyclohexanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DEHMLOW, Henrietta; MARTIN, Rainer E.; MATTEI, Patrizio; OBST SANDER, Ulrike; RICHTER, Hans; WO2013/60653; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

PREPARATION 1: 1 – Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde; Step a: 4-(/ert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester:; [00160] To a 50 mL flask was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (5.0 g; 29.0 mmol), imidazole (2.37 g; 34.8 mmol), DMF (30 mL) and ter/-buryldimethylsilyl chloride (4.81 g; 32.0 mmol). The solution was stirred for 78h at 20 0C. The reaction was diluted with EtOAc (100 mL), washed with water 2 x 100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude oil was purified by flash chromatography (silica gel, hexanes/EtOAc 1:0 to 1:1) to give pure product (7.79 g, 94% yield) as a 2:1 mixture of diastereomers.1H-NMR (400 MHz, CDCl3) (J = Hz) delta mixture 4.12 (m; 2H), 3.90 (m; 0.65H), 3.58 (m; 0.35H), 2.23 (m; IH), 1.98 (m; 3H), 1.82 (m; 3H), 1.49 (m; 2H), 1.21 (m; 3H), 0.88 (s; 9H), 0.05 (s; 3H), 0.03 (s; 3H). 13C-NMR (400 MHz, CDCl3) delta mixture 175.7, 175.6, 70.5, 66.6, 60.1, 60.0, 42.2, 42.1, 34.8, 32.8, 27.2, 25.8, 25.6, 23.4, 18.2, 18.0, 14.2, -4.7, -4.9. MS (ES+) m/z 287.22 [MH+].

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

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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. HPLC of Formula: C9H16O3

Step A: ethyl 4-iodocyclohexanecarboxylateTo a solution of ethyl 4-hydroxycyclohexane carboxylate (10.0 g, 58.1 mmol) inCH2C12 (200 mL) at 0 C was added imidazole (1 1.86 g, 174.0 mmol), triphenylphosphine (25.9 g, 99.0 mmol), and followed by iodine (25.05 g, 99.0 mmol) several portions over a period of 45 min. The resulting suspension was gradually allowed to warm up to rt. After stirring at rt over night, the mixture was partitioned between Et20 (200 mL) and water (200 mL). The organic layer was washed with saturated Na2S203 ( 100 mL) and brine (3×1 OOmL), dried over MgS04, and concentrated. The residue was purified by flash chromatography (Biotage 40+M) using 10- 20% EtOAc hexane gradient, affording the title compound: .H NMR (500 MHz, CDC13) delta 5.70 (m, IH), 4.20-4.10 (m, 2H), 2.58 (m, IH), 2.48-1.60 (m, 8H), 1.28 (mf 3H).

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; NARGUND, Ravi; LO, Michael Man-Chu; YAN, Lin; HUO, Pei; FRANKLIN, Christopher; WO2011/53519; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 3618-04-0, 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (10.32 g, 59.92 mmol) in dimethylformamide (50 mL) was added imidazole (8.16 g, 119.8 mmol), followed by tert-butyldimethylsilyl chloride (9.94 g, 65.9 mmol). The resulting mixture was stirred at room temperature for 16 hours. Diethyl ether was added (150 mL), and the mixture was washed with 1M [HC1] (150 mL). The aqueous layer was extracted with diethyl ether (150 mL). The combined organic layers were washed with 1M [HC1] (100 mL) and saturated sodium chloride solution (100 mL), dried over magnesium sulfate, filtered and concentrated to afford a clear oil. MS (CI) m/z 287 (M+1) [+]

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

tert-Butyldimethylchlorosilane (9.71 g, 64.45 mmol) was added portion wise to ethyl 4- hydroxycyclohexanecarboxylate (CAS no. 17159-80-7) (10 g, 58 mmol) and imidazole (7.9 g, 116 mmol) in DMF (58 mL) under nitrogen. The resulting solution was stirred at room temperature for 18 hours. The reaction mixture was diluted with diethyl ether (250 mL), and washed with saturated brine (500 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford the product (16.3 g). This was used without any further purification.IH NMR (300 MHz, CDCl3) delta 0.02 – 0.07 (5H, m), 0.87 – 0.90 (9H, m), 0.92 (IH, s), 1.22 – 1.29 (3H, m), 1.30 – 1.54 (3H, m), 1.59 – 1.70 (2H, m), 1.87 – 2.04 (3H, m), 2.21 – 2.32 (IH, m), 3.70 – 3.89 (IH, m), 4.07 – 4.16 (2H, m).

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 3618-04-0

(1) Synthesis of ethyl 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxylate To a solution of 25 g of 4-hydroxycyclohexanecarboxylic acid in 125 ml of N,N-dimethylformamide were sequentially added 21.7 g of imidazole and 39.6 ml of tert-butyl (diphenyl)silyl chloride under cooling with ice, followed by stirring the reaction mixture at room temperature for 3 hours. To the reaction mixture was added water and extracted with hexane. The resulting hexane solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

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; Iwasawa, Yoshikuzu; Kato, Tetsuya; Kawanishi, Nobuhiko; Masutani, Kouta; Mita, Takashi; Nonoshita, Katsumasa; Ohkubo, Mitsuru; US2008/58347; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics