Nitromethane → Methyl 3-methyl-4-nitrobutanoate

Participants

Reaction Steps

3 g (29.9 mmol) of trans-2-butenoic acid methyl ester and 0.69 g (5.99 mmol) of tetramethylguanidine and 9.14 g (149 mmol) of nitromethane were mixed. The resulting mixture was stirred at room temperature for 24 days. 100 mL of ethylacetoacetate was added to the solution and the reaction solution was washed with water, then an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 5.7 g (23.6 mmol) of the title compound in a yield of 100%.

Provenance & Evidence