Dimethyl Sulfate → HCID 86659132, compound

Participants

Reaction Conditions

Reaction Steps

The crude material containing 2-(2-(3-nitrophenyl)acetyl)malononitrile was dissolved in H2O (7 mL) and 1,4-dioxane (42 mL), to which NaHCO3 (11.5 g, 138 mmol) and dimethyl sulfate (10.5 mL, 110 mmol) were added. The reaction mixture was heated to 80° C. and left stirring for 12 hours. The reaction mixture was diluted with EtOAc (100 mL) and brine (100 mL). The aqueous portion was extracted with EtOAc (3×100 mL). The combined organic fractions were dried over MgSO4, filtered, and concentrated in vacuo. The recovered solid was purified by silica gel chromatography (100% chloroform). Fractions containing the desired enol ether were pooled, concentrated, and dissolved in hot MeOH. The solution was cooled and fine white crystals formed overnight, which were recovered by filtration and washed with ice cold MeOH to afford 2-(1-methoxy-2-(3-nitrophenyl)ethylidene)malononitrile. 1H NMR (400 MHz, DMSO): δ 7.78 (1H, d), 7.72 (t, 1H), 8.22 (d, 1H), 8.25 (s, 1H), 4.36 (s, 2H), 4.04 (s, 3H).

Provenance & Evidence