Water → 2-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylsulfonyl)propan-2-ol

HRID 1180590노트

반응식

HRID 1180590 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[NH:7][C:6]([C:15]([OH:26])([CH3:25])[CH2:16][S:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)=[CH:5]2.[OH:27]OS([O-])=O.[K+].[OH2:33]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[C:11]([F:12])([F:13])[F:14])[NH:7][C:6]([C:15]([OH:26])([CH3:25])[CH2:16][S:17]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)(=[O:27])=[O:33])=[CH:5]2

참가 물질

6

반응물 3

HCID 962Water2회HCID 23707502Potassium hydroxy sulfiteHCID 444191882-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylthio)propan-2-ol

생성물 1

HCID 116978032-(5-chloro-6-(trifluoromethyl)-1H-indol-2-yl)-1-(4-fluorophenylsulfonyl)propan-2-ol

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(5-chloro-6-trifluoromethyl-1H-indol-2-yl)-1-(4-fluoro -phenylsulfanyl)-propan-2-ol (0.42 g, 1.04 mmol) in dichloromethane (10 mL) was added water (10 mL). The solution was stirred rapidly and tetrabutylammonium hydrogensulfate (12 mg, 0.035 mmol) was added followed by OXONE® (1.02 g, 1.66 mmol). The reaction mixture turned bright yellow and was allowed to proceed overnight at room temperature. The reaction mixture was diluted with water and dichloromethane, the layers were separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water, twice with 10% sodium thiosulfate soluton and brine, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated and pre-absorbed onto silica gel and purified by column chromatography eluting with 80% diethyl ether/pentane to yield the title product as a solid.

후처리

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with water, twice with 10% sodium thiosulfate soluton and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe magnesium sulfate was filtered off
  6. concentrationthe filtrate was concentrated
  7. custompre-absorbed onto silica gel
  8. custompurified by column chromatography
  9. washeluting with 80% diethyl ether/pentane

출처 및 근거

ORD 기록
ord-ca4e5f46ccbe43b1a794d800cb514da3
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282507B2

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