تفاعل #6352

معادلة التفاعل

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

المردود 90.0%

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

المردود 90.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىby acid hydrolysis
2. 2
   أخرىA white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   ترشيحthe reaction mixture was filtered
5. 5
   أخرىthe filtrate evaporated
6. 6
   أخرىThe residue was partitioned between ethyl acetate and water
7. 7
   أخرىthe organic layer separated
8. 8
   غسيلwashed with saturated brine
9. 9
   تجفيفdried (MgSO4)
10. 10
    ترشيحfiltered
11. 11
    أخرىevaporated
12. 12
    أخرىto give a colourless oil

الإجراء التجريبي

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%).

المصدر