反应详情

Sodium metal (0.09 g) was dissolved in absolute ethanol (2 ml) under nitrogen. A solution of methyl (4-bromo-2-nitrophenyl)acetate (Intermediate 54) (1.0 g) in ethanol (8 ml) was treated with isoamyl nitrite (0.6 ml) followed by the solution of sodium ethoxide, yielding a black mixture. The mixture was stirred at 60° for 90 min then left at room temp. for 18 h. 2N Hydrochloric acid (20 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (×2) and brine, dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified on a Varian Bond-Elut SPE cartridge eluting with cyclohexane:ethyl acetate (100:0 to 97:3) to give the title compound as a cream coloured solid (577 mg).

1. customyielding a black mixture
2. waitthen left at room temp. for 18 h
3. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
4. washThe combined organic extracts were washed with water (×2) and brine
5. customdried
6. concentrationconcentrated under vacuum
7. customThe residue was purified on a Varian Bond-Elut SPE cartridge
8. washeluting with cyclohexane:ethyl acetate (100:0 to 97:3)