Pempidine → Butyl hept-2-ynoate

Participants

Reaction Steps

3.25 g (2.75 mmol) of tetrakis(triphenylphosphine)palladium(0) are introduced into 250 ml of dichloromethane in a 500 ml round-bottomed flask under argon. The dark brown solution is stirred at room temperature for 1 h. Then 150 mg (1.25 mmol) of 4-dimethylaminopyridine, 21.5 g (137.5 mmol) of 1,2,2,6,6-pentamethylpiperidine and 10.25 g (125 mmol) of 1-hexyne are added and heated to reflux at 40° C. Subsequently, 17 g (125 mmol) of n-butyl chloroformate are added dropwise over the course of 60 min. After a reaction time of 24 h, the reaction mixture is worked up by distillation to isolate n-butyl 2-heptynoate in 90% yield.

Provenance & Evidence