Nitromethane → 3-Hexanone, 6-nitro-

Participants

Reaction Conditions

Reaction Steps

A solution of sodium methoxide in MeOH (4.6M, 6.46 mL, 29.7 mmol, 0.25 equiv) was added to a solution of ethyl vinyl ketone (11.78 mL, 119 mmol, 1 equiv) and nitromethane (19.3 mL, 357 mmol, 3 equiv) in MeOH (30 mL, 3 vol) at −30° C. The reaction mixture was then warmed to −10° C. for 1.5 h, quenched with half saturated ammonium chloride solution (100 mL), and then extracted with dichloromethane (3×100 mL). The combined organics were dried over sodium sulfate, concentrated and then stripped from toluene (2×100 mL) and MeOH (100 mL) to provide 15.2 g of approximately 95% pure 6-nitro-hexan-3-one as determined by 1H NMR.

Provenance & Evidence