Acetic Acid → HCID 178469765, compound

Participants

Reaction Conditions

Reaction Steps

6-tert-Butyl-4-oxo-4H-pyran-3-carboxylic acid ethyl ester (300 mg, 1.34 mmol, prepared according to the literature procedure by McCombie, S. W. et al. J. Org. Chem. 1991, 56, 4963-4967) and ammonium acetate (300 mg, 4.16 mmol) were combined in ethanol/water (8 mL/3 ml). Acetic acid was added and reaction mixture was heated at 95° C. for 30 min. It was concentrated and basified with aqueous sodium hydroxide and extracted with methylene chloride (2×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 6-tert-butyl-4-hydroxy-nicotinic acid ethyl ester as a white solid (230 mg, 76%). LR-MS: 224 [(M+H)+]

Provenance & Evidence