反応 #64169

反応方程式

NH4Cl

(2S)-1,1,1-Trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol

3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-4,4,4-trifluoro-2-butanone

NaBH4

→

title compound

(S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

溶媒

methanol

反応条件

後処理

1. 1
   抽出The mixture was extracted with dichloromethane
2. 2
   その他the combined organic layers were dried
3. 3
   その他evaporated
4. 4
   その他The resulting solid was pre-absorbed onto silica gel
5. 5
   その他purified by chromatography, with ether

実験手順

(2S)-1,1,1-Trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol. To a stirred, cooled 0° C. solution of 3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-4,4,4-trifluoro-2-butanone (3.7 g, 10 mmol) in 135 mL methanol was added NaBH4 (1.7 g, 44 mmol). The mixture was stirred for 15 minutes. 100 mL of saturated aqueous NH4Cl was added. The mixture was extracted with dichloromethane and the combined organic layers were dried and evaporated. The resulting solid was pre-absorbed onto silica gel and purified by chromatography, with ether:hexane as the eluent (75:25), to give the title compound as a mixture of isomers (3.13 g, 83%); NMR (CDCl3): 7.96-7.89 (m,4, Ar), 7.58-7.49 (m,3, Ar), 7.48-7.39 (d,2, Ar), 3.91-3.86 (m,2), 3.13 (s,1), 3.08 (s,1), 2.80 (s,1), 2.76-2.75 (d,1), 2.68 (s,1), 1.47 (s,3, CH3); MS: m/z=375(M+1).

出典