Imidazole → 3-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrile

To a solution of 3-cyanophenol (5 g, 42 mmol) and imidazole (6.3 g, 92 mmol) in N,N-dimethylformamide (85 mL) at 0° C. was added (1,1-dimethylethyl)dimethylsilylchloride (7.6 g, 50 mmol). After stirring 10 min, the reaction was warmed to room temperature and stirred for 24 h. The solvent was removed in vacuo and the residual oil was partitioned between water (100 mL) and diethyl ether (300 mL). The separated diethyl ether layer was washed with water (3×100 mL) and brine (100 mL), then was dried (MgSO4) and filtered. The filtrate was evaporated under reduced pressure and the residue was flash chromatographed (silica gel, 50% ethyl acetate in petroleum ether) to yield 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzonitrile (9 g, 92% yield) as an oil.

1. stirringstirred for 24 h
2. customThe solvent was removed in vacuo
3. customthe residual oil was partitioned between water (100 mL) and diethyl ether (300 mL)
4. washThe separated diethyl ether layer was washed with water (3×100 mL) and brine (100 mL)
5. dry with materialwas dried (MgSO4)
6. filtrationfiltered
7. customThe filtrate was evaporated under reduced pressure
8. customchromatographed (silica gel, 50% ethyl acetate in petroleum ether)

ORD record

ord-b47a98aa5b4449a19db9a7b885789f17

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515124B2