Hexane → HCID 67789227, compound

Participants

Reaction Conditions

Reaction Steps

In an argon stream, a solution of trans-3-(1-hydroxyethyl)-4-vinyl-2-azetidinone (0.10 g) in dry tetrahydrofuran (10 ml) is cooled to -75° C. and a commercial n-butyllithium (1.6M)-hexane solution (0.9 ml) is added dropwise to the solution while maintaining a temperature at -65° C. or lower. The mixture is stirred at -75° C. for an hour and a solution of tert-butyldimethylsilyl chloride (0.16 g) in dry tetrahydrofuran (2 ml) is added dropwise at -70° C. or lower. The reaction mixture is further stirred at -73° C. for 0.5 hour and poured into a mixture of ethyl acetate (70 ml), water (50 ml) and acetic acid (2 ml). The organic layer is separated, adjusted to pH 7.0 with aqueous sodium hydrogen carbonate, washed with aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to give 0.1 g of trans-3-(1-hydroxyethyl)-1-(tert-butyldimethylsilyl)-4-vinyl- 2-azetidinone.

Provenance & Evidence