Реакция #6352

Уравнение реакции

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

Выход 90.0%

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

Выход 90.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   Другоеby acid hydrolysis
2. 2
   ДругоеA white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   Фильтрацияthe reaction mixture was filtered
5. 5
   Другоеthe filtrate evaporated
6. 6
   ДругоеThe residue was partitioned between ethyl acetate and water
7. 7
   Другоеthe organic layer separated
8. 8
   Промывкаwashed with saturated brine
9. 9
   Сушкаdried (MgSO4)
10. 10
    Фильтрацияfiltered
11. 11
    Другоеevaporated
12. 12
    Другоеto give a colourless oil

Методика

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%).

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