M-Cresol → tert-Butyl(dimethyl)(3-methylphenoxy)silane

Participants

Reaction Steps

To a solution of 3-hydroxytoluene (2 g, 8.5 mmol) in 20 mL of CH2Cl2 is added DBU (3.32 mL, 22.2 mmol) and 1,1-dimethylethyl)dimethylsilyl chloride (3.07 g, 20.34 mmol). After 1.5 hours, the solution is diluted with EtOAc. The organic solution is washed with 1 N HCl, 10% Na2CO3 and saturated NaCl. The organic layer is dried over MgSO4, filtered, and concentrated. The crude product is purified by column chromatography eluting with 5% EtOAc/hexanes to afford the title compound (4.1 g, 18.5 mmol) as an oil.

Provenance & Evidence