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

HRID 35891ノート

反応式

HRID 35891 の反応式
[F:1][C:2]([F:25])([F:24])[C@@:3]([CH3:23])([OH:22])[CH:4](O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.OC(C)(C(F)(F)F)C(=O)CC1C=CC(S(C2C=CC=CC=2)(=O)=O)=CC=1.[BH4-].[Na+].[NH4+].[Cl-]>CO>[F:25][C:2]([F:1])([F:24])[C@:3]([OH:22])([CH3:23])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)(=[O:14])=[O:13])=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 19939314HCID 19939314、化合物HCID 57137960(2S)-1,1,1-Trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol

生成物 1

HCID 67708369(S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

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).

後処理

  1. extractionThe mixture was extracted with dichloromethane
  2. customthe combined organic layers were dried
  3. customevaporated
  4. customThe resulting solid was pre-absorbed onto silica gel
  5. custompurified by chromatography, with ether

出典と根拠

ORDレコード
ord-ba261498cc284b2f81434134316e6102
出典データセット
uspto-grants-1995_05
特許番号
US05411973

反応ノート

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