Реакция #6127

Уравнение реакции

trichloroacetonitrile

NaH

2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose

→

expected product

Выход 53.0%

2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate

Выход 53.0%

Растворители

methylene chloride

Условия реакции

Обработка

1. 1
   Фильтрацияthe reaction medium is filtered on silica in methylene chloride
2. 2
   Другоеpurified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent

Методика

1.5 ml (15.10-3 mol) of trichloroacetonitrile and 70 mg of NaH (2.3.10-3 mol of NaH in 80% dispersion) are added to a solution of 1 g (3.42.10-3 mol) of 2, 3, 4 -tri-O-acetyl-5-thio-α-D-xylopyranose in 10 ml of methylene chloride. After 4 h at room temperature, the reaction medium is filtered on silica in methylene chloride and then purified by chromatography on silica gel using a hexane/ethyl acetate mixture (3/1 v/v) as the eluent. 790 mg (yield: 53%) of the expected product are obtained after crystallization from an ethyl acetate/hexane mixture.

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