Reaktion #6352

Reaktionsgleichung

imidazole

t-butyldiphenylsilyl chloride

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

acetic acid

→

title compound

Ausbeute 90.0%

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

Ausbeute 90.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby acid hydrolysis
2. 2
   SonstigeA white precipitate formed immediately
3. 3
   workup.WAITAfter 2 hours
4. 4
   Filtrationthe reaction mixture was filtered
5. 5
   Sonstigethe filtrate evaporated
6. 6
   SonstigeThe residue was partitioned between ethyl acetate and water
7. 7
   Sonstigethe organic layer separated
8. 8
   Waschenwashed with saturated brine
9. 9
   Trocknendried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated
12. 12
    Sonstigeto give a colourless oil

Vorschrift

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%).

Quelle