Dimethylformamide → HCID 12795068, compound

Participants

Reaction Steps

A solution of 17 g. of methyl N-(3-iodopropyl)-3-carbomethoxypyrrole-2-acetate is added portionwise over an hour to a stirred suspension of 52.7 g. (99%) NaH in 300 ml. dry dimethylformamide at 0° C. and maintained in nitrogen. The temperature is allowed to reach 20° and stirring is continued for 1 hour. The reaction mixture is diluted with saturated NaCl and extracted with benzene 4 times. The combined extracts are washed with water, dried over sodium sulfate and evaporated to dryness in vacuo. Recrystallization of the residue using benzene-hexane affords dimethyl 5,6,7,8-tetrahydropyrrolo[1,2-a]-pyridine-1,8-dicarboxylate (VII, R=H, n=1) m.p. 108° C.

Provenance & Evidence