反应详情

A solution of 2-fluoro-4-nitrobenzonitrile (0.541 g, 2.43 mmol) in methanol (20 mL) and hydrochloric acid (3 mL, 6 N) was hydrogenated (55 psi) over 10% palladium on carbon (164 mg) overnight. The reaction mixture was filtered and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 mL) and treated with 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (0.517 mg, 2.10 mmol) and triethylamine (0.6 mL, 4.3 mmol). After 16 h at rt, the reaction mixture was diluted with dichloromethane and washed with sodium bicarbonate solution and brine, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes) to give 1-63A-(0.287 g, 60%) as a colorless oil which solidified on standing.

1. filtrationThe reaction mixture was filtered
2. concentrationconcentrated under reduced pressure
3. dissolutionThe residue was dissolved in tetrahydrofuran (5 mL)
4. washwashed with sodium bicarbonate solution and brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes)
8. customto give 1-63A-(0.287 g, 60%) as a colorless oil which