Реакция #2028893

Уравнение реакции

aldehyde

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

sodium borohydride

→

desired product

Выход 46.0%

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

Выход 46.0%

Растворители

methanol

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was quenched with the addition of an aqueous 1M KHSO4 solution (3 mL)
2. 2
   ЭкстракцияThe mixture was extracted with dichloromethane
3. 3
   Другоеthe organic solution dried
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеThe residue was chromatographed on silica (1:1 hexane:ethyl acetate)

Методика

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).

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