Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → HCID 86721217, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (3 g, 13.5 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (2.152 mL, 16.20 mmol) in toluene (10 ml) was stirred at 90° C. for 14 hr. The reaction mixture was concentrated under reduced pressure, and ethanol (15 mL) was added thereto. To the residue were added tert-butylhydrazine monohydrochloride (1.85 g, 14.85 mmol) and TEA (2.07 mL, 14.85 mmol), and the mixture was stirred at 80° C. for 20 hr. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added thereto. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→60% ethyl acetate/hexane) to give ethyl 1-tert-butyl-5-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate (2.86 g, 9.46 mmol, 70.1%) as a pale-yellow powder.

Provenance & Evidence