Benzaldehyde → HCID 58951927, compound

Participants

Reaction Steps

To a solution of 0.30 g (1.71 mmol) 1-(dimethylsulfamoyl)-imidazole in 10 ml tetrahydrofuran were added 1.2 ml (1.88 mmol) of a 1.6M butyl lithium solution in hexane at −75° C. After stirring for 15 min 0.30 g (2 mmol) tert-butyldimethylsilyl chloride was added at −75° C. and the mixture was stirred at ambient temperature for 2 h. The mixture was cooled down again to −75° C. and 1.2 ml (1.88 mmol) of a 1.6M butyl lithium solution in hexane were added. After stirring for 30 min 0.22 ml (2.14 mmol) benzaldehyde was added at −75° C. and the mixture was allowed to reach room temperature overnight. The mixture was partitioned between water and dichloromethane, re-extracted with dichloromethane and the combined organic layers are dried over MgSO4, filtered and evaporated to yield 0.73 g of an yellow oil, that was used directly in the next step, MS (EI): 338.1 ((M-tBu)+.).

Provenance & Evidence