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

HRID 623428노트

반응식

HRID 623428 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>CN(C)C(=O)C>[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 N,N-dimethylacetamide (54 mL) is stirred at room temperature for 4 hours. The reaction mixture is poured into water (100 mL) and extracted with n-hexane/ethyl acetate (1:10, 100 mL). The organic layer is washed with water (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (5:1) to give 1.14 g (45% yield) of the title compound as colorless oil.

후처리

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

출처 및 근거

ORD 기록
ord-cda06d7b6082405999f359872291792b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302991B2

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