Hydrochloric Acid → HCID 13560307, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-acetoxy-7-hydroxymethyl-3,4-dihydrobenzopyran acetate (1.00 g, 3.78 mmol) in dry dimethylformamide (5 mL) was added a solution of potassium p-acetylthiophenoxide (720 mg, 3.8 mmol) in dimethylformamide (5 mL). The mixture was heated at 50° C. for 2.25 hours, then poured into ice water (75 mL). Sodium hydroxide (10% aqueous, 20 mL) was added, then mixture allowed to stir for 30 minutes, then acidified with 2N hydrochloric acid and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with 7% NaHCO3, and brine (2x), dried (Na2SO4) and concentrated. The crude product was purified by preparative HPLC (30% ethyl acetate hexane as eluant and recrystallized from ethyl acetate hexane to afford 6-hydroxy-7-(4-acetylphenyl)thiomethyl-3, 4-dihydrobenzopyran as a white solid (172 mg), m.p. 192°-193° C.

Provenance & Evidence