Diazomethane → HCID 59364065, compound

Participants

Reaction Steps

A solution of methyl (2E)-3-(4-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy}phenyl)acrylate (1.50 g, 3.26 mmol) in tetrahydrofuran (50 mL) was stirred under ice-cooling, and a solution of diazomethane prepared from N-methyl-N′-nitro-N-nitrosoguanidine (50% water-containing product, 4.98 g, 16.9 mmol) and 9.5 M aqueous potassium hydroxide solution (12.0 mL, 114 mmol) in diethyl ether (25 mL), and palladium(II) acetate (36.6 mg, 0.163 mmol) were alternately added thereto over 10 min in small portions. The reaction mixture was stirred for 5 hr, and acetic acid (3 drops) was added. The insoluble material was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (1.53 g, yield 99%) as a colorless oil.

Provenance & Evidence