反应详情

A solution of 2-(4-chloro-benzenesulfonylmethyl)-1,3,4-trifluoro-benzene (5.6 g, 17.5 mmol) in THF/TMEDA (5:1, 180 mL) at −78° C. was treated with n-BuLi (12 mL, 17.5 mmol, 1.5 M in hexanes). After 15 min, a solution of N-p-toluenesulfonyl aziridine (3.5 g, 17.5 mmol, prepared as described in Eur. J. Org. Chem. 2002, 3004) in THF (10 mL) was added, and the reaction mixture warmed slowly to ambient temperature. After 4 h, the reaction mixture was quenched with 1N HCl and extracted with EtOAc (2×). The combined organic extracts were washed with saturated aqueous NaHCO3, brine, dried over MgSO4 and concentrated in vacuo. Flash chromatography (25→50% EtOAc/Hex) provided the title compound (4.9 g, 54%): 1H NMR (CDCl3 400 MHz) δ 7.64 (d, J=8.1 Hz, 2H), 7.57 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 7.28 (d, J=8.1 Hz, 2H), 7.14 (m, 1H), 6.75 (m, 1H), 4.81 (m, 1H), 3.17 (ddd, J=7.1, 7.1, 5.6 Hz, 1H), 2.96 (m, 1H), 2.64 (m, 1H), 2.47 (m, 1H), 2.41 (s, 3H).

1. waitAfter 4 h
2. customthe reaction mixture was quenched with 1N HCl
3. extractionextracted with EtOAc (2×)
4. washThe combined organic extracts were washed with saturated aqueous NaHCO3, brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo