Nitromethane → 3-Hexanone, 6-nitro-

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Reaction Conditions

Reaction Steps

To ethylvinylketone (41.4 g, 493 mmol) in MeOH (150 mL) and nitromethane (160 mL) was added sodium methoxide (ca. 123 mmol; 27 mL of a 25% solution in MeOH). The mixture was warmed to −10° C. over 30 min. After 1.5 h at −10° C., the mixture was quenched with saturated NH4Cl (250 mL) and water (250 mL). The mixture was pured into a separatory funnel and the lower organic layer was removed. The aqueous portion was extracted with CH2Cl2 (2×250 mL) and the combined organic portions were dried with MgSO4 and concentrated. The resultant liquid was reconcentrated from toluene (2×250 mL) followed by methanol (1×250 mL) to yield the desired material.

Provenance & Evidence