Water → HCID 22161779, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyltriphenyl phosphonium bromide (11.85 g) in tetrahydrofuran (100 ml), n-butyl lithium (10.2 ml) was added dropwise with stirring in nitrogen flow at -40° C. The temperature was raised to -20° C. over 30 minutes, a solution of 8-(t-butyldimethylsilyloxymethyl)-4-oxo-1-ethyl-1,2,3,4-tetrahydroquinoline (3.8 g) in tetrahydrofuran (100 ml) was added dropwise thereto. The temperature was raised gradually to the room temperature, the mixture was stirred for 2.5 hours. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane and dried, then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (8:1)]to give 8-(t-butyldimethylsilyloxymethyl)-4-methylene-1-ethyl-1,2,3,4tetrahydroquinoline (3.4 g).

Provenance & Evidence