Reacción #6352

Ecuación de reacción

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

Rendimiento 90.0%

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

Rendimiento 90.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroby acid hydrolysis
2. 2
   OtroA white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   Filtraciónthe reaction mixture was filtered
5. 5
   Otrothe filtrate evaporated
6. 6
   OtroThe residue was partitioned between ethyl acetate and water
7. 7
   Otrothe organic layer separated
8. 8
   Lavadowashed with saturated brine
9. 9
   Secadodried (MgSO4)
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated
12. 12
    Otroto give a colourless oil

Procedimiento

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%).

Fuente