Hydrochloric Acid → HCID 11687622, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromomethyl-2-(4-hydroxyphenyl)chromen-4-one (250 mg, 0.754 mmol) in dioxane:DMF (10:2, 12 mL), was added potassium acetate (500 mg, 3.77 mmol). The mixture was heated at 100° C. for 3 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give crude product (225 mg, 96%). To a solution of the crude product (220 mg, 0.711 mmol) in MeOH:THF (5 mL:5 mL) was added K2CO3 (216 mg, 1.56 mmol) and the mixture was stirred for 24 h at rt. Then the reaction mixture was neutralized by dilute HCl and extracted by EtOAc, the combined organic layers were washed with water, brine, dried and concentrated to give a crude product, which was purified by column chromatography using 5% MeOH in dichloromethane, to afford 6-hydroxymethyl-2-(4-hydroxyphenyl)chromen-4-one (80 mg, 42%). MS (ES) m/z: 269.88 (M+1), 268.85 (M); Mp. 246-247° C.

Provenance & Evidence