Water → HCID 66652045, compound

Participants

Reaction Steps

Heat a solution of [2-(3-methoxyphenyl)-cyclopentyl]-acetic acid ethyl ester (4.2 g, 16.0 mmoles) in polyphosphoric acid (27 g) at 100° C. for 3.5 hours. Cool the reaction to r.t. and add ice, water and methylene chloride cautiously. Extract the aqueous layer was 2× with additional methylene chloride, combine the organic layers and dry over anhydrous sodium sulfate. Concentrate in vacuo at 40° C. Chromatograph the crude product on silica with 11-17% ethyl acetate/hexanes to yield the titled compound (2.8 g, 81%) as a neat crystalline solid. 1H NMR (CDCl3): 7.95 (d, J=8.8 Hz, 1H), 6.8 (dd, J=2.8 Hz, 6.4 Hz, 1H), 6.73(m, 1H), 3.86 (s, 3H), 3.19 (m, 1H), 2.72 (m, 1H), 2.53 (m, 2H), 2.18 (m, 1H), 2.0-1.75 (m, 5H).

Provenance & Evidence