Tetrahydrofuran → 5-Ethynylnicotinonitrile

Participants

Reaction Steps

Add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (50.0 mL, 50.0 mmol) to a suspension of 5-trimethylsilanylethynyl-nicotinonitrile (10.0 g, 50.0 mmol), (prepared as described in PREPARATION 3), in triethylamine (98 mL) at 0° C. After 5 min, dilute the reaction mixture with ethyl acetate and wash twice with water. Back-extract the combined aqueous washes twice with ethyl acetate. Wash the combined organic layers with a saturated aqueous solution of sodium chloride, dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with a gradient from 98:2 to 90:10 dichloromethane:ethyl acetate, to give the title compound as a white crystalline solid (4.75 g, 74%).

Provenance & Evidence