Hydrochloric Acid → HCID 178497301, compound

Participants

Reaction Steps

According to the method described in Eur. J. Med. Chem. 36 (2001) 697, a solution of 1-[2-hydroxy-4-(methoxymethoxy)-3-methylphenyl]propan-1-one (3.99 g, 17.8 mmol) obtained in Example 2-1 and carbon disulfide (1.07 mL, 17.8 mmol) in tetrahydrofuran (30 mL) was added to a solution of potassium t-butoxide (5.99 g, 53.4 mmol) in tetrahydrofuran (20 mL), and the mixture was stirred overnight at room temperature. Water (50 mL) was added to the reaction solution, and then the pH of the mixture was adjusted to 5 with 2 M hydrochloric acid, followed by extraction with ethyl acetate. The pH of the aqueous layer was adjusted to 5 again with 2 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and then dried over magnesium sulfate. The solvent was concentrated under reduced pressure to obtain 3.80 g of the title compound (yield: 80%).

Provenance & Evidence