Dimethylformamide → HCID 68431573, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (60% in mineral oil, 0.33 g, 8.3 mmol) in dry DMF (20 mL) was stirred and cooled to 0° C., and di-tert-butyl malonate (1.5 g, 7.1 mmol) was added. The mixture was allowed to warm to room temperature before addition of 4,5-difluoro-2-methoxybenzonitrile (1.0 g, 5.9 mmol). The mixture was heated at 80° C. for 4 h with stirring, then the reaction mixture was cooled to room temperature and poured into a mixture of ice-water (100 mL) and AcOEt (100 mL). The layers were separated, and the organic layer was washed successively with water, and brine, then dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes, 0->10%) to give the di-tert-butyl (4-cyano-5-fluoro-2-methoxyphenyl)propanedioate. LCMS: [(M+1)−t-Bu, CO2−t-Bu]+=210.1; tR=2.2 min.

Provenance & Evidence