methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Base Information

Chemical Name:methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate
CAS No.:467242-36-0
Molecular Formula:C₁₇H₂₁F₃O₅S
Molecular Weight:394.412
Hs Code.:

Synonyms:methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

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Chemical Property of methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

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Technology Process of methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

There total 12 articles about methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

: 358-23-6
trifluoromethylsulfonic anhydride

: 467242-40-6
methyl (1R)-1-[2-(1-methyl-2-oxocyclopentyl)ethyl]cyclohexa-2,5-diene-1-carboxylate

: 467242-36-0
methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Guidance literature:: With 2,6-di-tert-butyl-pyridine; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4039(02)00570-1

Reference yield:

: 30889-20-4
methyl cyclohexa-2,5-diene-1-carboxylate

: 467242-36-0
methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 83 percent / DMPU / tetrahydrofuran / -78 - 50 °C

2.1: 78 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

3.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

3.2: 95 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

4.1: 79 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 15 h / 20 °C

With n-butyllithium; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 3.1: Swern oxidation;
DOI:10.1002/ejoc.200600429

Reference yield:

: 7424-82-0,99031-95-5,94089-46-0
methyl (1R)-3-(1-methyl-2-oxocyclopentyl)propanoate

: 467242-36-0
methyl (1R)-1-[2-(1-methyl-2-{[(trifluoromethyl)sulfonyl]oxy}cyclopent-2-en-1-yl)ethyl]cyclohexa-2,5-diene-1-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / potassium hydroxide / methanol / 16 h / 20 °C

2.1: 84 percent / iodine; Pb(OAc)4 / CCl₄ / 1 h / 80 °C / Irradiation

3.1: 65 percent / NaBH₄ / ethanol / 3 h / 20 °C

4.1: 96 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

5.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: 83 percent / DMPU / tetrahydrofuran / -78 - 50 °C

6.1: 78 percent / n-tetrabutylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

7.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -78 °C

7.2: 95 percent / Et₃N / CH₂Cl₂ / 8 h / 20 °C

8.1: 79 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 15 h / 20 °C

With 1H-imidazole; lead(IV) acetate; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; hexane; dichloromethane; 2.1: Barton-Koch reaction / 7.1: Swern oxidation;
DOI:10.1002/ejoc.200600429