(4-Fluorobenzyl)triphenylphosphonium chloride → HCID 68831952, compound

Participants

Reaction Steps

4-fluorobenzyltriphenyl phosphonium chloride (1.22 g, 3 mmole) was suspended under argon in abs. THF (15 ml) and cooled to −5° C. Potassium-tert-butanolate (337 mg, 3 mmole) dissolved in THF (14 ml) was added dropwise and the mixture post-stirred for 30 min at <0°. 4-dimethylamino-4-phenylcyclohexane carbaldehyde (467 mg, 2 mmole) dissolved in THF (8 ml) was subsequently added dropwise and the mixture stirred for 20 h with gradual heating to RT. For working up, the mixture was evaporated and 15 ml 1M HCl, 5 ml water and 30 ml ether were added to the residue. After stirring for 60 min, between the aqueous phase and the organic phase, there was a white solid which was suction filtered and washed with ether (3×2 ml). Following analysis and DC, this solid was the hydrochloride of the least polar of four possible diastereoisomers of {4-[2-(4-fluorophenyl)vinyl]-1-phenylcyclohexyl}dimethylamine (145 mg, mp. 255 to 258° C.).

Provenance & Evidence