Sodium hydride → (3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

Participants

Reaction Steps

To a suspension of sodium hydride (a 60% oil suspension, 3.47 g, 86.8 mmol) in THF (150 mL) was added m-benzenedimethanol (10.00 g, 72.4 mmol) at room temperature, and stirred for 1 hour. To the resulting cloudy liquid was added t-butyldimethylchlorosilane (10.91 g, 72.4 mmol) at room temperature, and stirred for another 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with a 10% aqueous potassium hydrogensulfate solution and extracted three times with ethyl acetate. The ethyl acetate extract solution was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by a silica gel column chromatography (silica gel 400 mL; hexane/ethyl acetate=5/1 to 2/1) to obtain the title compound (9.25 g, 51%) as a colorless oil.

Provenance & Evidence