反応 #6352

反応方程式

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

収率 90.0%

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

収率 90.0%

溶媒

THF

反応条件

後処理

1. 1
   その他by acid hydrolysis
2. 2
   その他A white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   ろ過the reaction mixture was filtered
5. 5
   その他the filtrate evaporated
6. 6
   その他The residue was partitioned between ethyl acetate and water
7. 7
   その他the organic layer separated
8. 8
   洗浄washed with saturated brine
9. 9
   乾燥dried (MgSO4)
10. 10
    ろ過filtered
11. 11
    その他evaporated
12. 12
    その他to give a colourless oil

実験手順

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%).

出典