Hydrochloric Acid → HCID 23563768, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-bromophenyl)-2-(3-cyclopentyloxy-4-methoxyphenyl) acetaldehyde (2.60 g, 6.7 mmol) in THF (10 ml) was added methyl vinyl ketone (670 ul, 8.4 mmol). The solution was stirred at −10° C. and 10% ethanolic potassium hydroxide (480 ul) was added slowly. After 0.5 h the reaction mixture was warmed to room temperature and stirred for additional 1 h. Water and ethyl acetate were added and the mixture was neutralized with 3N hydrochloric acid. The layers were separated and the aqueous layer washed twice with ethyl acetate. The combined organic extract was washed with water then brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (silica gel, 12% ethyl acetate/82% hexane) provided the title compound as a pale white waxy solid (1.39 g, 47%). MS (m/e): 441 [(M+1)+], 443 [(M+3)+].

Provenance & Evidence