Reacción #2028893

Ecuación de reacción

aldehyde

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

sodium borohydride

→

desired product

Rendimiento 46.0%

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

Rendimiento 46.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente