Réaction #2028893

Équation de réaction

aldehyde

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

sodium borohydride

→

desired product

Rendement 46.0%

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

Rendement 46.0%

Solvants

methanol

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source