Reacción #42734

Ecuación de reacción

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture was then partitioned between 200 mL of saturated sodium chloride and 200 mL of diethyl ether
2. 2
   ExtracciónThe aqueous layer was extracted with 200 mL of diethyl ether
3. 3
   Lavadowashed with saturated sodium chloride (3×100 mL)
4. 4
   Secadodried over MgSO4
5. 5
   Concentraciónconcentrated
6. 6
   OtroThe product was purified by silica gel chromatography
7. 7
   Lavadoeluting with hexanes
8. 8
   Concentraciónconcentrated

Procedimiento

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.

Fuente