Diethyl Oxalate → HCID 86619021, compound

Participants

Reaction Steps

To a suspension of potassium ethoxide (2.21 g, 26.3 mmol) in diethyl ether (20 mL) was added diethyl oxalate (3.57 mL, 26.3 mmol) under a nitrogen atmosphere. The reaction exhibited a slight exotherm and the reaction mixture was stirred for 20 min. The heterogeneous mixture became a homogeneous orange solution and then became a heterogeneous thick slurry and the stirring was ceased. In a separate container 2-(dibenzylamino)-5-nitro-4-methylpyridine (8.76 g, 26.3 mmol) was diluted with diethyl ether (14.3 mL) to give a suspension. The suspension was added to the slurry obtained above. The mixture was manually stirred using a glass rod, then sonicated for 20 min resulting in a thick black heterogeneous solution. The reaction mixture was allowed to stand under a nitrogen atmosphere overnight. The resulting solid was collected by filtration and rinsed with diethyl ether to give potassium (1Z)-1-[2-(dibenzylamino)-5-nitropyridin-4-yl]-3-ethoxy-3-oxoprop-1-en-2-olate (9.5 g, 76%) as a deep red solid: 1H NMR (300 MHz, CD3OD) δ1.17 (3H, t, J=7.0 Hz), 3.58 (2H, q, J=6.9 Hz), 4.82 (4H, s), 7.22-7.32 (11H, m), 8.74 (1H, s), 8.80 (1H, s).

Provenance & Evidence