1,2-Dimethoxyethane → HCID 66712110, compound

Participants

Reaction Steps

Into a 1-Neck round-bottom flask, 4-Cyano-4-(3-methoxy-4-nitro-phenyl)-heptanedioic acid dimethyl ester (4.20 g, 11.5 mmol), 1,2-Dimethoxyethane (80 mL, 800 mmol), and Sodium Hydride (60% dispersion mineral oil)(6:4, Sodium hydride:Mineral Oil, 1.38 g, 34.6 mmol) were added, and heated to reflux overnight. The reaction was cooled to room temperature. Water was added to quenched the excess NaH. 2N HCl was added to adjust pH to 2. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc. The collected fractions afforded 5-Cyano-5-(3-methoxy-4-nitro-phenyl)-2-oxo-cyclohexanecarboxylic acid methyl ester as an off white solid (2.00, 59%).

Provenance & Evidence