反応 #2028893

反応方程式

aldehyde

4-[4-formyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

sodium borohydride

→

desired product

収率 46.0%

4-[4-hydroxymethyl-5-phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide

収率 46.0%

溶媒

methanol

反応条件

後処理

1. 1
   その他The reaction was quenched with the addition of an aqueous 1M KHSO4 solution (3 mL)
2. 2
   抽出The mixture was extracted with dichloromethane
3. 3
   その他the organic solution dried
4. 4
   濃縮concentrated
5. 5
   その他The residue was chromatographed on silica (1:1 hexane:ethyl acetate)

実験手順

To a solution of the aldehyde prepared in Step 2 (165 mg, 0.41 mmol) in methanol (3.5 mL) at 0° C. was added sodium borohydride (16 mg, 0.41 mmol). The reaction solution was kept at 0° C. for 2.5 hours. The reaction was quenched with the addition of an aqueous 1M KHSO4 solution (3 mL). The mixture was extracted with dichloromethane and the organic solution dried and concentrated. The residue was chromatographed on silica (1:1 hexane:ethyl acetate) to give the desired product (36 mg, 46%): m.p. 179°-180° C.; 1H NMR d 7.91 (m, 2H), 7.53-7.40 (m, 5H), 6.75 (s, 2H), 4.53 (d, 2h, J=5.0 Hz), 4.30 (t, 1H, J=5.0 Hz).

出典