反应详情

温度

-78 °C

To a solution of 12.96 g (60 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 52.35 mL (123 mmol) 2.35M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 4.64 mL (60 mmol) of N,N-dimethylformamide dropwise. The reaction mixture was allowed to warm to room temperature and stir for ca. 2 hours. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes) affording 5.72 g of the title compound as a white solid, m.p. 101.5°-103° C. 1H NMR (CDCl3, 200 MHz.) δ: 10.25(s,1H), 6.81(d,1H), 6.6(d,1H), 4.93(bs,1H), 3.98(s,3H), 1.27(s,9H).

1. additionwas added dropwise
2. temperatureto warm to room temperature
3. stirringstir for ca. 2 hours
4. temperatureThe reaction mixture was cooled to 0° C.
5. customThe THF phase was separated
6. washwashed with brine
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customThe crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes)