Dimethylformamide → 3-Formyl-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro [3,2-b]-pyridin-2(4H)-one

Participants

Reaction Steps

With ice-cooling, 1.89 ml (24.56 mmol) of N,N-dimethylformamide and 0.28 ml (3.02 mmol) of phosphoryl chloride are initially charged, and after one hour 500 mg (1.89 mmol) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one (1-2) are added. The mixture is then stirred at room temperature for two hours. The reaction mixture is then made alkaline using sodium carbonate, and the precipitated solid is filtered off and washed with water. This gives 0.33 g (56% of theory) of 3-formyl-4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one.

Provenance & Evidence