Triethylamine → N-[4'-(tert-butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide

Participants

Reaction Steps

Oxalyl chloride (4.3 g, 33 mmol) is added to a solution of (4-chlorophenyl-prop-2-ynyloxy-acetic acid (6.8 g, 30 mmol) in a mixture of 150 ml of dichloromethane and few drops of N,N-dimethylformamide. The reaction mixture is stirred for 4 hours at room temperature and then added to a solution of 4′-(tert-butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-ylamine (13.8 g, 30 mmol) and triethylamine (4.6 g, 45 mmol) in 150 ml of dichloromethane. The resulting mixture is stirred for 16 hours at room temperature under a nitrogen atmosphere. Subsequently, the mixture is diluted with chloroform and extracted with water. The combined organic layer is dried over sodium sulfate and evaporated and the remaining crude product is subjected to flash-chromatography (ethyl acetate/hexane 3;7) yielding N-[4′-(tert-butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-yl]-2-(4-chlorophenyl)-2-prop-2-ynyloxy-acetamide as an orange oil.

Provenance & Evidence