Water → HCID 57672423, compound

Participants

Reaction Steps

(S)-methyl 3-(4-hydroxyphenyl)hept-4-ynoate 24.1 was prepared by a method based on that reported in U.S. Patent Application Publication No. 2006/0004012 which is hereby incorporated by reference. To a stirred solution of 24.1 (0.077 g, 0.3 mmol) in EtOAc (3 mL) at 23° C. was added quinoline (0.08 mL, 0.7 mmol), followed by Lindlar Catalyst (0.004 g, 0.03 mmol). The reaction was placed under an atmosphere of hydrogen and then stirred at room temperature. After 15 hours, water was added to the mixture, and the mixture was extracted with EtOAc. After concentration, the residue was purified on silica gel (0%-20% EtOAc/hexane) to give (R,Z)-methyl 3-(4-hydroxyphenyl)hept-4-enoate 34.1 (0.073 g, 94%). MS ESI (pos.) m/e: 235.1 (M+H)+.

Provenance & Evidence