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Cesium carbonate → 2-Chloro-4-methyl-5-(2,2,2-trifluoroethoxyl)pyridine

HRID 715417
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HRID 715417 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:22][C:23]([F:26])([F:25])[F:24])(=O)=O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:9])[C:5]([O:8][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:6][N:7]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 712995492-Chloro-5-hydroxy-4-methylpyridine

생성물 1

HCID 898739752-Chloro-4-methyl-5-(2,2,2-trifluoroethoxyl)pyridine수율 95.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 6-chloro-4-methylpyridin-3-ol (2.00 g, 13.9 mmol) and cesium carbonate (6.81 g, 20.9 mmol) in DMF (40 mL) is added dropwise 2,2,2-trifluoroethyl trifluoromethanesulfonate (3.56 g, 15.3 mmol) at 0° C. After stirring at rt for 1 hour, the mixture is poured onto water (300 mL). The aqueous layer is extracted with EtOAc (300 mL). The separated organic layer is washed with water (200 mL), dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (9:1) to give 3.00 g (95% yield) of the title compound as white solid.

후처리

  1. additionthe mixture is poured onto water (300 mL)
  2. extractionThe aqueous layer is extracted with EtOAc (300 mL)
  3. washThe separated organic layer is washed with water (200 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (9:1)

출처 및 근거

ORD 기록
ord-b55b27342eed4d93852f583a1fd4dd76
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187475B2

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