Methanol → HCID 67217792, compound

Participants

Reaction Steps

To a solution of ethyl ester of example 17.3 (493 mg) in 10 ml THF:water (4:1) was added sodium hydroxide (68 mg). The reaction mixture was stirred at room temperature for 3 hours before adding 2 ml of methanol. The reaction was stirred overnight before evaporation of the solvent in vacuo. The aqueous layer was extracted with ethyl acetate before being acidified. It was then extracted several times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford a mixture of regioisomeric acids (224 mg, 3-methyl major and 5-methyl minor). 1H-NMR (CDCl3, 400 MHz): 8.5 (s, 1H), 7.5 (m, 2H), 7.45 (m, 1H), 4.35 (d, 1H), 3.85 (d, 1H), 2.50 (s, 3H).

Provenance & Evidence