Acetone → HCID 58636773, compound

Participants

Reaction Steps

Sulfuric acid (18.71 g, 0.1908 mole, 10 ml) was added to a solution of 6-cyclopropyl-4,5-bis-hydroxymethyl-2-methyl-pyridin-3-ol (166) (10.0 g, 47.7 mmol) in anhydrous acetone (60 mL) at 0° C. The reaction mixture was slowly warmed to room temperature and stirred overnight, poured into a cold solution of aqueous sodium hydroxide (excess) and the crude product was extracted with chloroform and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified on a silica gel column using a mixture of ethyl acetate hexane (2:8) as eluant to give (6-cyclopropyl-2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-methanol (167) (5.2 g, 44% yield) as a brown liquid.

Provenance & Evidence