Dimethyl acetylenedicarboxylate → HCID 13154893, compound

Participants

Reaction Steps

A solution of azidomethyl-trimethyl-silane (5.0 g, 38.69 mmol) and dimethyl acetylenedicarboxylate (4.74 mL, 38.69 mmol) in benzene (200 mL) was refluxed for 2 h. The solvent was removed in vacuo and the resultant crude material was diluted with water (100 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and 20% ethyl acetate/hexane) as colorless liquid (10 g, 36.9 mmol, 95.2%).

Provenance & Evidence