Triethylamine → HCID 12018132, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (1.05 eq., 4.15 mL) was added dropwise to a solution of N-methylindole (5.8 mL, 50 mmol) in diethyl ether (395 mL) at 0° C. Yellow precipitates were formed. After the completion of the addition, the reaction mixture was stirred at 0° C. for 30 min., and then the volatiles were removed under vacuo. The residue was re-dissolved in dichloromethane (375 mL) and added to a solution of 3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenylacetic acid (13.3 g, 50 mmol) and Et3N (12.5 mL, 2.2eq.) in dichloromethane (375 mL) at 0° C. The resulting mixture was stirred at 0° C. and then allowed to warmed up slowly to room temperature. After stirring overnight, the volatiles were removed and the residue was purified on a silica gel column with dichloromethane to give 3-(1-methylindol-3-yl)-4-{3-((R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyloxy)phenyl]furan-2,5-dione (5.4 g, 27% yield).

Provenance & Evidence