反应详情

To a solution of (R)-3-benzyloxypropane-1,2-diol (prepared from (S)-4-benzylymethyl-2,2-dimethyl-1,3-dioxolane (commercially available from FLUKA) by acid hydrolysis using 80% aqueous acetic acid), (8.3 g, 47.2 mmol) in dry THF (70 ml) was added imidazole (6.42 g, 94.4 mmol). After 2 minutes, t-butyldiphenylsilyl chloride (12.28 ml, 47.2 mmol) was added. A white precipitate formed immediately. After 2 hours, the reaction mixture was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate and water, the organic layer separated, washed with saturated brine, dried (MgSO4), filtered and evaporated to give a colourless oil. Chromatography of the oil on silica gel (dichloromethane as eluant) afforded the title compound as a colourless oil (17.72 g, 90%).

1. customby acid hydrolysis
2. customA white precipitate formed immediately
3. waitAfter 2 hours
4. filtrationthe reaction mixture was filtered
5. customthe filtrate evaporated
6. customThe residue was partitioned between ethyl acetate and water
7. customthe organic layer separated
8. washwashed with saturated brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. customevaporated
12. customto give a colourless oil