Water → Ethyl 2-(4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)butanoate

HRID 2390317노트

반응식

HRID 2390317 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[C:15]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:19])=[O:18])[CH:14]=[CH:13][C:12]=2[CH3:23])[CH:3]=1.Br[CH:25]([CH2:31][CH3:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C([O-])([O-])=O.[K+].[K+].O>COCCOC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:25]([CH2:31][CH3:32])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[C:15]([S:17]([CH2:20][CH2:21][CH3:22])(=[O:19])=[O:18])[CH:14]=[CH:13][C:12]=2[CH3:23])[CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79039Butanoic acid, 2-bromo-, ethyl esterHCID 565939734-Chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenol2회

생성물 1

HCID 58522053Ethyl 2-(4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)butanoate

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenol (Intermediate 267; 110 mg; 0.32 mmol) and ethyl 2-bromobutyrate (50 μl; 0.35 mmol) in DME (2 mL) was treated with K2CO3 (250 mg, 1.81 mmol) and refluxed for 18 hours. Water was added and the reaction mixture was extracted with EtOAc. The organic phase was dried over MgSO4, filtered, concentrated and purified by flash column chromatography (silica), eluting with heptane containing increasing amounts of EtOAc. The title compound was obtained as a colorless sticky solid which was not further purified before use.

후처리

  1. temperaturerefluxed for 18 hours
  2. extractionthe reaction mixture was extracted with EtOAc
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica)
  7. washeluting with heptane containing
  8. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-60c01326f7dc4fbdb41d61683042fa7e
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273769B2

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