Water → Methyl 6-(2,2,2-trifluoroethoxy)picolinate

HRID 715376

반응식

HRID 715376 반응식
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][CH:6]=1.CI.[C:18](=O)([O-])[O-].[K+].[K+].O>CC(N(C)C)=O>[F:15][C:2]([F:1])([F:14])[CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]([O:13][CH3:18])=[O:12])[CH:8]=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 212530416-(2,2,2-Trifluoroethoxy)pyridine-2-carboxylic acid

생성물 1

HCID 67510684Methyl 6-(2,2,2-trifluoroethoxy)picolinate수율 45%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

A mixture of 6-(2,2,2-trifluoroethoxy)picolinic acid (2.40 g, 10.9 mmol, Step-1), methyl iodide (3.39 mL, 54.3 mmol) and potassium carbonate (4.50 g, 32.6 mmol) in DMA (54 mL) is stirred at rt for 4 hours. The reaction mixture is poured into water (100 mL) and extracted with n-hexane/EtOAc (1:10, 100 mL). The organic layer is washed with water (100 mL), dried over sodium sulfate. After filtration, the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1) to give 1.14 g (45% yield) of the title compound as colorless oil.

후처리

  1. extractionextracted with n-hexane/EtOAc (1:10, 100 mL)
  2. washThe organic layer is washed with water (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (5:1)

출처 및 근거

ORD 기록
ord-42f4fbfe8b3d4762b2a71549f26a57a4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187475B2

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