تفاعل #2028893

معادلة التفاعل

aldehyde

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

sodium borohydride

→

desired product

المردود 46.0%

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

المردود 46.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر