HCID 86629740, compound → HCID 86629741, compound

Participants

Reaction Steps

A solution of (±)-4-ethyl 1-methyl 2-(4-fluoro-2,6-dinitrophenyl)succinate from Step C (7.23 g, 21.0 mmol) and iron powder (5.86 g, 105 mmol) in EtOH (60 mL) and saturated aqueous NH4Cl (15 mL) was stirred at reflux for 4.5 h. The warm reaction mixture was filtered through Celite, rinsing the filter cake with ethyl acetate. The crude product solution was washed with saturated aqueous NaHCO3 (300 mL). The layers were separated and the aqueous layer was further extracted with EtOAc (2×200 mL). The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 50:50, to give the title compound. MS: m/z=253 (M+1).

Provenance & Evidence