Methanol → Methyl 3-cyclopentyl-2-(4-methylsulfonylphenyl)propionate

HRID 1860137Notes

Reaction equation

[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21]O>S(=O)(=O)(O)O>[CH3:21][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid (500 mg, 1.89 mmol) in methanol (15 mL) was treated slowly with concentrated sulfuric acid (3 drops). The resulting reaction mixture was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/3 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-methanesulfonyl-phenyl)propionic acid methyl ester (377 mg, 72%) as a white solid: mp 63-66° C.; EI-HRMS m/e calcd for C16H22O4S (M+) 310.1239, found 310.1230.

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureunder reflux for 15 h
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3182eb9fa5b14669a4adccc3c3710943
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528543B1

Reaction notes

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