Potassium Carbonate → 7-(2-Trimethylsilylethylthio)-4-(3-furyl)coumarin

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-4-(furan-3-yl)coumarin (Coumarin 4) (1.5 g, 5.15 mmol), 2-(trimethylsilyl)ethanethiol (830 mg, 6.18 mmol), and K2CO3 (1.77 g, 12.9 mmol) in 1-methyl-2-pyrrolidinone (12 mL) was heated at 105° C. for 4 h. After cooling, there was added saturated aqueous NH4Cl (10 mL), then H2O (50 mL) and the mixture was extracted twice with EtOAc. The organic extracts were washed 4 times with H2O, dried over MgSO4 and evaporated to a residue which was chromatographed on silica gel eluting with a 1:3 mixture of EtOAc and hexane, to afford the title compound (963 mg) as a tan solid.

Provenance & Evidence