反应详情

A solution of 4-benzyloxy-3-benzyloxymethylbutan-1-ol (41.75 g, 139 mmol) in 150 ml of dry dichloromethane was cooled in ice-water bath. Triphenylphosphine (42.0 g, 160 mmol) was added with stirring and then N-bromosuccinimide (26.0 g, 146 mmol) in portions during 15 min. After 1 h at room temperature ether (400 ml) was added and the precipitated triphenylphosphine oxide filtered off. The solution was concentrated in vacuum to a small volume, and more ether was added to extract the product from precipitated triphenylphosphine oxide. Finally, this extraction-precipitation step was repeated with light petroleum to give, after evaporation, 33.55 g (66%) of crude title compound.

1. filtrationthe precipitated triphenylphosphine oxide filtered off
2. concentrationThe solution was concentrated in vacuum to a small volume, and more ether
3. additionwas added
4. extractionto extract the product
5. customfrom precipitated triphenylphosphine oxide
6. customFinally, this extraction-precipitation step
7. customto give
8. customafter evaporation, 33.55 g (66%) of crude title compound