Ethylene Glycol → HCID 178466006, compound

Participants

Reaction Steps

At -10° C. and under an atmosphere of protective gas, 250 ml of ethylene glycol were added to 1.5 g (62.3 mmol) of sodium hydride. The mixture was warmed to room temperature, 12.5 g (31.2 mmol) of methyl 2,4-dichloro-3-[N-(4-methylphenylsulfonylamino)iminomethyl]benzoate were added and the mixture was heated at 85° C. for 15 minutes. After cooling, the diazo compound was extracted with diethyl ether or ethyl acetate, the combined organic phases were washed with 10% strength aqueous sodium hydroxide solution and water and dried and a large part of the solvent was removed. 4.7 g (68.6 mmol) of 3-butyn-2-one were subsequently added and the mixture was heated at 80° C. for 2.5 hours. The mixture was stirred at room temperature for 48 hours and then washed with water, dried and concentrated. The residue was chromatographed over silica gel (eluent: cyclohexane/ethyl acetate=1/1). 5.75 g (54% of theory) of 2-hydroxyethyl 2,4-dichloro-3-(3-methylcarbonyl-1H-pyrazol-5-yl)benzoate were obtained.

Provenance & Evidence