Dimethylformamide → HCID 20739786, compound

Participants

Reaction Conditions

Reaction Steps

A three-necked flask having an inner volume of 500 ml equipped with a thermometer and a reflux condenser was charged with 22.3 g (0.1 mol) of N-ethylcarbazole-3-carboxaldehyde, 39 g (0.11 mol) of methyltriphenyl phosphonium bromide and 150 ml of N,N-dimethylformamide. This mixture was cooled by an ice-methanol bath to −5° C. under nitrogen gas stream while stirring the mixture by a magnetic stirring bar. To the mixture was gradually added 30 ml of 28% sodium methoxide methanol solution dropwise while maintaining the temperature of the mixture below 5° C. Then, the resultant mixture was stirred for 1 hour at 10° C., stirred for 2 hours at room temperature, poured into 3 L of cold water to deposite a crude solid, and filtered to obtain the crude solid. The crude solid was washed with water and dried, and the residue was purified by a silica gel column chromatography (dissolution medium: hexane/ethyl acetate=5/1). The dissolution medium was distilled off from the fraction containing the desired product and the resultant oil was subjected to crystallization using iso-propanol, to obtain 21 g of N-ethyl-3-vinylcarbazole as a crystal.

Provenance & Evidence