Sodium Bicarbonate → HCID 72297485, compound

Participants

Reaction Steps

Bring 1-(5,6-dimethoxy-3-nitropyridin-2-yl)-2-nitroethanol, 7 (173 mg, 0.63 mmol) and NaOAc (208 mg, 2.53 mmol) to reflux in Ac2O (5.0 mL), following the reaction by LC-MS. After 45 min, pour the reaction mixture onto an ice/H2O mixture, neutralize with NaHCO3, extract with EtOAc, wash with saturated NaHCO3, dry (MgSO4) and concentrate. Purify the raw product by flash chromatography (EtOAc at 20%/heptane) to give 8 (144 mg, 89.2%) as an ivory-colored solid, which is an 8:2 mixture of isomers: 1H NMR (CDCl3) δ 8.68 (d, 0.8 H, J=12.9 Hz), 8.57 (d, 1.6 H, J=13 Hz), 7.99 (d, 0.83 H, J=12.9 Hz), 7.72 (d, 1H, J=11.7 Hz), 7.3 (d, 0.15 H, J=12 Hz), 4.18 (s, 2.6 H), 4.15 (s, 0.56 H), is 4.05 (s, 2.8 H), 3.97 (0.54 H); Rf (EtOAc at 40%/heptane, two spots)=0.4 and 0.42; m/z obs.=256 (M+1).

Provenance & Evidence