Hydrochloric Acid → 4-(3-Fluorophenyl)-3-buten-1-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.0 g of (3-hydroxypropyl)triphenylphosphonium bromide and 20 ml of tetrahydrofuran was cooled to 0° C., to which 12.5 ml of 1.6M n-butyl lithium (as a hexane solution) was slowly added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes, to which a mixture of 1.24 g of 3-fluorobenzaldehyde and 10 ml of tetrahydrofuran was slowly added dropwise at the same temperature, followed by further stirring at room temperature for 6 hours. The reaction mixture was poured into ice-water, acidified by the addition of 10% hydrochloric acid, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with saturated saline solution, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.70 g of 4-(3-fluorophenyl)-3-buten-1-ol.

Provenance & Evidence