Triethylamine → HCID 86610167, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl anthranilate (5.54 g, 36.6 mmol), triethylamine (3.48 g, 34.5 mmol), cuprous chloride (0.21 g, 2.15 mmol), copper powder (0.163 g, 2.56 mmol) in H2O (4 mL) and THF (14 mL) was added 3-chloro-3-methyl-1-butyne (2.21 g, 21.6 mmol). After heating to 65° C. for 4 h the reaction was cooled, diluted with water and extracted using diethyl ether (three times). The combined organic layers were washed with water, dried using MgSO4 and concentrated under vacuum. Purification by silica gel chromatography (5% EtOAc/hexanes-10% EtOAc/hexanes) afforded the desired product.

Provenance & Evidence