Tetrahydrofuran → HCID 86747310, compound

Participants

Reaction Steps

n-Butyl-lithium (1.6M in hexane, 1.375 ml) was added dropwise to a solution of methyltriphenylphosphonium bromide (0.786 g) in a mixture of THF (15 ml) and diethyl ether (2 ml). The mixture was stirred at ambient temperature for 2 hours. The solution so obtained was added dropwise to a solution of 4-(3-benzyloxyphenyl)-4-formyltetrahydropyran (0.592 g) in diethyl ether (10 ml) and the mixture was stirred at ambient temperature for 4 hours. The mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p 40°-60° C.) and ethyl acetate as eluent. There was thus obtained 4-(3-benzyloxyphenyl-4-vinyltetrahydropyran (0.407 g, 70%), as an oil.

Provenance & Evidence