반응 #6352

반응 방정식

imidazole

t-butyldiphenylsilyl chloride

(R)-3-benzyloxypropane-1,2-diol

acetic acid

→

title compound

수율 90.0%

(S)-1-Benzyloxy-3-(t-butyldiphenylsilyloxy)propan-2-ol

수율 90.0%

용매

THF

반응 조건

후처리

1. 1
   기타by acid hydrolysis
2. 2
   기타A white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   여과the reaction mixture was filtered
5. 5
   기타the filtrate evaporated
6. 6
   기타The residue was partitioned between ethyl acetate and water
7. 7
   기타the organic layer separated
8. 8
   세척washed with saturated brine
9. 9
   건조dried (MgSO4)
10. 10
    여과filtered
11. 11
    기타evaporated
12. 12
    기타to give a colourless oil

실험 절차

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%).

출처