Imidazole → 4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-carbonitrile

Participants

Reaction Steps

A solution of 4-(4-hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (5 g, 25 mmol), t-butyldimethylsilyl chloride (4.46 g, 29 mmol) and imidazole (2.34 g, 34 mmol) were stirred in DMF (15 ml) at room temperature. After 30 minutes, a yellow suspension was observed. The reaction was partitioned between ether (75 ml) and water (100 ml). The ether was then washed further with water (4×50 ml), dried over sodium sulphate, filtered and concentrated in vacuo. The title compound was isolated as a pale orange waxy solid (7 g, 90%).

Provenance & Evidence