HCID 23293613, compound → HCID 70133496, compound

Participants

Reaction Steps

A mixture of ethyl 2-bromo-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthyl)acetate (2.2 g, 7.0 mmol), 1N potassium tert-butoxide in tetrahydrofuran (14 mL, Aldrich) and tert-butanol (140 mL) was stirred for 5 h at room temperature. The resulting suspension was concentrated in vacuo, diluted with water (200 mL) and washed with diethyl ether. The aqueous layer was acidified by adding 1N hydrochloric acid (14 mL) and extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and chromatographed on Silica Gel 60 using ethyl acetate-hexane (1:1) as eluent. The fractions containing only (E)-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)acetic acid were combined and concentrated in vacuo to give a white solid (0.8 g, 55%); NMR (DMSO-d6): d 12.22 (br s, 1H, COOH), 7.57 (d of d, Jm =2.6 Hz, Jo =11.0 Hz, 1H, Ar), 7.12-7.28 (m, 2H, Ar), 6.36 (s, 1H, =CH, E), 3.04 (t, 2H, ArCH2), 2.74 (t, 2H, CH2), 1.74 (m, 2H, CH2); steady-state nOe: irradiation at 6.36, observed 25% nOe at 7.57.

Provenance & Evidence