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

HRID 35891노트

반응식

HRID 35891 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-ba261498cc284b2f81434134316e6102
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411973

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