Diethyl Ether → HCID 54104552, compound

Participants

Reaction Steps

To a suspension of pyridinium dichromate (0.38 g, 1.0 mmol) and acetic anhydride (0.4 mL, 4.2 mmol) in dichloromethane (15 mL) was rapidly added a solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-4-[(N-propan-2-ol)-carboxamido]-1-phenylbut-1-yne (0.59 g, 1.4 mmol) in dichloromethane (5 mL) and the reaction was refluxed under an argon atmosphere for 7 h, then at room temperature for 3 d. The reaction was diluted with ether (30 mL), was filtered through Celite and was evaporated. Purification by flash chromatography, eluted with 1:1 ethyl acetate:hexanes provided the title compound (0.38 g, 64%) as a pale yellow solid, mp 105-106° C.

Provenance & Evidence