Oxalyl chloride → Ethyl 3-methylpyrazine-2-carboxylate

Participants

Reaction Steps

To a solution of 3-methyl-pyrazine-2-carboxylic acid (10 g) (commercially available) and N,N-dimethylformamide (“DMF”) (1 drop) in dichloromethane (20 ml) at ambient temperature was added drop wise oxalyl chloride (2.57 ml). The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and the residue dissolved in dichloromethane (20 ml). Triethylamine (4.04 ml) was added to this solution followed by drop wise addition of ethanol (10 ml). The reaction mixture was stirred at ambient temperature for one hour and then concentrated. The residue was purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in iso-hexane) to give 3-methyl-pyrazine-2-carboxylic acid ethyl ester (9.85 g). MH+=167, RT=0.73 min (Method A). 1H-NMR (400 MHz, CDCl3): 8.61 (d, 1H), 8.54 (d, 1H), 4.49 (q, 2H), 2.85 (s, 3H), 1.46 (t, 3H) ppm.

Provenance & Evidence