Ammonium Chloride → 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol

Participants

Reaction Steps

To a solution of (trimethylsilyl)acetylene (23.75 ml) in tetrahydrofuran (250 ml) was added a 1.6M solution of butyllithium in hexane (105 ml) below -60° C. After stirring for one hour, a solution of 2-(N-allyloxycarbonyl-N-benzylamino)acetaldehyde (32.86 g) in tetrahydrofuran (30 ml) was added to the mixture below -60° C. The solution was stirred at the same condition for one hour and an aqueous saturated ammonium chloride (100 ml) was added to the reaction mixture below -60° C. After stirring at the ambient temperature for one hour, ethyl acetate (300 ml) was poured into the mixture. The solution was washed with brine (150 ml×2), dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (300 g) and eluted with a mixture of hexane and ethyl acetate (9:1, V/V) to give 1-(N-allyloxycarbonyl-N-benzylamino)-4-trimethylsilyl-3-butyn-2-ol (19.77 g) as a syrup.

Provenance & Evidence