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

HRID 646561노트

반응식

HRID 646561 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 solution 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 solution 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-5a1e8647a201435a9c6979e4bff1ff99
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705147B2

반응 노트

불러오는 중…