反应详情

To a solution of compound iii (3.26 g, 8.06 mmol) in dry THF (50 mL), LAH pallet (0.46 g, 12.10 mmol) was added at 0° C. The resulting reaction mixture was stirred for 4 h, quenched by the addition of water (5 mL), concentrated, diluted with ethyl acetate (50 mL), and washed, in tandem, with 1N HCl, water, 10% Na2CO3 aqueous solution, and brine. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate-hexane, 3:7) to afford 4-hydroxymethyl-N-(4-nitro-3-trifluoromethyl-phenyl)-benzenesulfonamide (iv) as light yellow solid with 71% yield. 1H NMR (300 MHz, CDCl3) δ 2.06 (br, 1H), 4.75 (s, 2H), 6.96 (br, 1H), 7.59 (d, J=10.17 Hz, 2H), 7.84 (d, J=8.19 Hz, 2H), 7.88 (d, J=8.43 Hz, 1H), 8.03 (d, J=8.43 Hz, 1H), 8.16 (s, 1H).

1. customThe resulting reaction mixture
2. customquenched by the addition of water (5 mL)
3. concentrationconcentrated
4. additiondiluted with ethyl acetate (50 mL)
5. washwashed, in tandem, with 1N HCl, water, 10% Na2CO3 aqueous solution, and brine
6. customThe organic layer was dried
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography (ethyl acetate-hexane, 3:7)