Tetrabutylammonium Fluoride → 4-(Hydroxymethyl)-6-methylpicolinonitrile

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Reaction Steps

4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridine-2-carbonitrile (8 g, 30.53 mmol) was stirred with 1M tetrabutylammonium fluoride in THF (32 ml, 32 mmol) in THF (30 ml) at room temperature. After 1 hr., the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (4:1)) to afford 4.07 g (90%) of 4-Hydroxymethyl-6-methyl-pyridine-2-carbonitrile as a white solid. m.p. 136-138° C.; 1H NMR (200 MHz, CDCl3) δ 2.59 (3H, s), 4.78 (2H, s), 7.39 (1H, s), 7.53 (1H, s).

Provenance & Evidence