Tetrabutylammonium Fluoride → beta-Methylenephenethyl alcohol

Participants

Reaction Steps

To a well stirred solution of tert-butyl-dimethyl-(2-phenyl-allyloxy)-silane (1.3 g, 5.23 mmol) in tetrahydrofuran (10 mL) is slowly added a solution of a 1 N tetrabutylammonium fluoride in tetrahydrofuran (10.5 mL, 10.5 mmol). The reaction is allowed to stir for 20 min, quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield 700 mg of the title compound.

Provenance & Evidence