Methanol → 5-(4-Fluoro-phenyl)-pentanoic acid methyl ester

Reaction equation

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

Participants

Reactant 4

HCID 887Methanol

HCID 962Water

HCID 24386Thionyl Chloride

HCID 27346705-(4-Fluorophenyl)pentanoic acid

Product 1

HCID 685705095-(4-Fluoro-phenyl)-pentanoic acid methyl esterYield 75%

Procedure

Thionylchloride (288 μl, 3.98 mmol) was added dropwise to a solution of 5-(4-fluoro-phenyl)-pentanoic acid (520 mg, 2.65 mmol) in methanol (11 ml) at −15° C. The reaction mixture was then stirred at room temperature for 1.5 h. Water was added and the mixture was extracted 3 times with diethylether. The combined extracts were washed with water and brine, dried (Na2SO4) and evaporated. The remaining residue was purified by column chromatography (silica gel, ethyl acetate/heptane 5:95 to 12:88) to obtain 5-(4-fluoro-phenyl)-pentanoic acid methyl ester (420 mg, 2 mmol; 75%) as colorless liquid. MS: m/e 211.0 [M+H+].