Dichloromethane → Benzyl [1-(4-nitrobenzyl)but-3-enyl]ethoxymethylcarbamate

Participants

Reaction Conditions

Reaction Steps

A mixture of 10 ml of 50% strength aqueous sodium hydroxide solution, 25 ml of methylene chloride and 130 mg (0.4 mmol) of benzyltributylammonium chloride is vigorously stirred at 5-10° C. Benzyl [1-(4-nitrobenzyl)but-3-enyl]carbamate (6.8 g, 20.0 mmol) is added in one portion followed by 2.64 g (28 mmol) of chloromethyl ethyl ether over a period of 2 hours. The mixture is then stirred at room temperature for 1 hour, diluted with ice and water and extracted with methylene chloride. The organic phase is dried over sodium sulfate, evaporated and chromatographed on silica gel (hexane/ethyl acetate (10:1)). The title compound is obtained as a colourless oil. TLC: ethyl acetate/hexane (1:3) Rf =0.41. FD-MS: M+ : 398.

Provenance & Evidence