HCID 86629740, compound → HCID 86629741, compound

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).

1. temperatureat reflux for 4.5 h
2. customThe warm reaction mixture
3. filtrationwas filtered through Celite
4. washrinsing the filter cake with ethyl acetate
5. washThe crude product solution was washed with saturated aqueous NaHCO3 (300 mL)
6. customThe layers were separated
7. extractionthe aqueous layer was further extracted with EtOAc (2×200 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. concentrationconcentrated in vacuo
10. customThe crude product was purified by silica gel chromatography
11. washeluting with a gradient of hexanes

ORD record

ord-879b6a1c28614ea8b49e0f3e765ad8a8

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947677B2