Benzaldehyde → HCID 10453483, compound

Participants

Reaction Steps

Camphorsulfonic acid is added to a solution of 7-nitro-heptan-4-one from preparation 2 in MeOH and trimethyl orthoformate and the resulting solution is stirred at room temperature for 30 min. A solution of ammonium acetate in MeOH and benzaldehyde is added and the solution is stirred at room temperature for 6 h. The reaction is then heated at 40° C. for 7 h. The reaction is cooled to 35° C. and stirred overnight, then is cooled to 30° C. for 4 h, and finally to room temperature. After stirring over a weekend, the reaction mixture is cooled to 0° C. The product is collected by filtration to afford benzylidene-(5,5-dimethoxy-2-nitro-1phenyl-octyl)-amine with only the cis nitrophenyl stereochemistry.

Provenance & Evidence