Tetrabutylammonium Fluoride → 3,5-Bis(hydroxymethyl)benzonitrile

Participants

Reaction Steps

To a solution of 3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile (1.45 g, 3.702 mmol) in tetrahydrofuran (30 mL) at room temperature was added tetrabutylammonium fluoride (9.255 mL, 9.255 mmol, 1 M in tetrahydrofuran). The reaction mixture was stirred at room temperature for 2 h then concentrated in vacuo. The residue was partitioned between ethyl acetate (20 mL) and water (30 mL). The layers were separated and the product was extracted with ethyl acetate (3×20 mL). The organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solid was filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 75% ethyl acetate in hexanes yielded 3,5-bis-hydroxymethyl-benzonitrile (465 mg, 77%).

Provenance & Evidence