Tetrabutylammonium Fluoride → 3-Hydroxymethyl-5-methoxymethyl-benzonitrile

Participants

Reaction Steps

To a solution of 3-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxymethyl-benzonitrile (1.402 g, 4.810 mmol) in tetrahydrofuran (10 mL) at room temperature was added tetrabutylammonium fluoride (5.051 mL, 5.051 mmol, 1 M in tetrahydrofuran). The reaction mixture was stirred at room temperature for 2 h then concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 40% ethyl acetate in hexanes yielded 3-hydroxymethyl-5-methoxymethyl-benzonitrile (713 mg, 84%).

Provenance & Evidence