Reaktion #42734

Reaktionsgleichung

product

(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethanol

imidazole

tert-butyldimethylsilyl chloride

→

title compound

[(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethoxy]-tert-butyldimethylsilane

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether
2. 2
   ExtraktionThe aqueous layer was extracted with 200 mL of diethyl ether
3. 3
   Waschenwashed with saturated sodium chloride (3×100 mL)
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe product was purified by silica gel chromatography
7. 7
   Wascheneluting with hexanes
8. 8
   Einengenconcentrated

Vorschrift

To the product of step (d) (10 g, 34.8 mmol) and imidazole (4.7 g, 69.7 mmol) dissolved in 100 mL DMF was added tert-butyldimethylsilyl chloride (5.78 g, 38.3 mmol). The reaction mixture was stirred for 18 hours. The reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether. The aqueous layer was extracted with 200 mL of diethyl ether. The organic layers were then combined, washed with saturated sodium chloride (3×100 mL), dried over MgSO4 and concentrated. The product was purified by silica gel chromatography, eluting with hexanes followed by 5% ethyl acetate in hexanes. The desired fractions were combined and concentrated to give the title compound as an oil.

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