Trifluoroacetic acid → (+/-) 3-(3,4-Dimethoxyphenyl)sulfanyl-7-phenylheptanoic acid

Participants

Reaction Steps

To a solution of t-butyl-3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoate (14.9 g, 0.03 mol) in CH2Cl2 (150 mL) cooled to 0° C., is added trifluoroacetic acid (30 mL). The solution is allowed to warm to room temperature and stir overnight after which TLC analysis indicated complete reaction. The reaction mixture is concentrated in vacuo and the brown residue is chromatographed on silica gel (pet-ether/EtOAc, 1:1) to afford 11.9 g of (±) 3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoic acid (91%) as a pale yellow oil. TLC analysis [pet-ether/EtOAc, 1:1, Rf (heptanoate)=0.95, Rf (acid)=0.15]. 1H NMR (300 MHz, CDCl3) δ 1.5-1.65 (m, 6H), 2.55 (m, 4H), 3.30 (t, 1H), 3.85, (d, 6H), 6.80 (d, 1H), 6.98-7.31 (m, 7H) ppm. Mass spectrum (FAB) m/z 374 M+.

Provenance & Evidence