2-phenylmethoxyethanesulfonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 28% ammonium hydroxide (10 ml) was added dropwise 2-(benzyloxy)ethanesulfonyl chloride (4.1 g) in dichloromethane (10 ml) over 10 minutes under ice-cooling. The mixture was stirred at ambient temperature overnight. The organic layer was separated and the aqueous layer was extracted with dichloromethane/methanol (5/1). The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/50) to give 2-(benzyloxy)ethanesulfonamide (1.6 g). cooling The organic layer was separated the aqueous layer was extracted with dichloromethane/methanol (5/1) The combined organic layer was dried over sodium sulfate evaporated under reduced pressure The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=50/50)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 2-(benzyloxy)ethanesulfonic acid (4.0 g) was added thionyl chloride (13.5 ml) dropwise at ambient temperature for 15 minutes and the mixture was stirred at the same temperature for 10 minutes. To the mixture was added dropwise N,N-dimethylformamide (0.072 ml) at ambient temperature. The mixture was stirred at the same temperature for 20 minutes and refluxed for 1 hour. After cooling down to room temperature, the mixture was evaporated under reduced pressure to give 2-(benzyloxy)ethanesulfonyl chloride (4.1 g). The mixture was stirred at the same temperature for 20 minutes refluxed for 1 hour the mixture was evaporated under reduced pressure