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

HRID 715389

反応式

HRID 715389 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

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), and 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.

後処理

  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)

出典と根拠

ORDレコード
ord-bf8c25c864af4104974e95365d7fd433
出典データセット
uspto-grants-2015_11
特許番号
US09187475B2

関連ノート

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