Methyl iodide → trans-Glutaconic acid methyl ester

Participants

Reaction Steps

To a stirring solution of glutaconic acid in DMF (0.1 M) at 0° C. was added NaH (1 eq). After 15 min, iodomethane (1.2 eq) was added, and the mixture was allowed to warm to room temperature overnight. The reaction was quenched with saturated ammonium chloride, and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (silica; 10% MeOH/CHCl3) to afford a colorless viscous oil. EI-MS m/z 143 (M−H)−

Provenance & Evidence