Nitromethane → HCID 10920798, compound

Participants

Reaction Steps

To 53.4 g (544 mmol) of 1-hexen-3-one in 250 mL of methanol and 294 mL (5440 mmol) of nitromethane was added as a slow, steady stream 30 mL (136 mmol) of 25% NaOMe in methanol. The resultant yellow solution was warmed to −5° C. over 1 h, and kept between −5° C. and −10° C. for an additional 3 h. The solution was warmed to 0° C. for 1 h and was then quenched with 250 mL of saturated NH4Cl. The mixture was diluted with 200 mL brine to aid in layer separation, and extracted with ether (2×250 mL). The combined ether extracts were washed with Brine, dried with MgSO4, filtered and concentrated to give 75.7 g (88%) of a yellow liquid. 1H NMR revealed the presence of ca. 10% of 7-nitro-trideca-4,10-dione arising from the combination of one molar equivallent of nitromethane with two molar equivallents of 1-hexen-3-one. The products are insepararable by silica gel chromatography (EtOAc/hexanes), so the material was generally used in the next step without purification. Title compound: mass spectrum m/e=144 (M−1).

Provenance & Evidence