Réaction #6352

Équation de réaction

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

Rendement 90.0%

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

Rendement 90.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autreby acid hydrolysis
2. 2
   AutreA white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   Filtrationthe reaction mixture was filtered
5. 5
   Autrethe filtrate evaporated
6. 6
   AutreThe residue was partitioned between ethyl acetate and water
7. 7
   Autrethe organic layer separated
8. 8
   Lavagewashed with saturated brine
9. 9
   Séchagedried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    Autreevaporated
12. 12
    Autreto give a colourless oil

Mode opératoire

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%).

Source