Potassium Carbonate → 2-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl ester

HRID 571684ノート

反応式

HRID 571684 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([F:24])([F:23])C([O-])=O.[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([O:11][CH:19]([F:24])[F:23])=[CH:7][N:6]=1)=[O:4]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 178498852HCID 178498852、化合物

生成物 1

HCID 578272862-Pyrazinecarboxylic acid, 5-(difluoromethoxy)-, methyl ester収率 20%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To 5-hydroxypyrazine-2-carboxylic acid methyl ester (2.0 g, 13 mmol) in a glass tube reaction vessel in DMF (26 mL) was added potassium carbonate (5.3 g, 39 mmol) and sodium 2-chloro-2,2-difluoroacetate (4.0 g, 26 mmol). The reaction vessel was capped and warmed to 100° C. The reaction was stirred for 30 minutes and cooled to room temperature. The reaction was filtered washing with EtOAc. The filtrate was concentrated in vacuo. The residue was taken up into EtOAc and washed with brine. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/hex) to give methyl-5-(difluoromethoxy)pyrazine-2-carboxylate (0.09 g, 0.46 mmol) (0.40 g, 20%).

後処理

  1. customThe reaction vessel was capped
  2. temperaturecooled to room temperature
  3. filtrationThe reaction was filtered
  4. washwashing with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. washwashed with brine
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography (0-40% EtOAc/hex)

出典と根拠

ORDレコード
ord-54a46a51e9eb40d1978da4ca3d3e3373
出典データセット
uspto-grants-2015_05
特許番号
US09029362B2

反応ノート

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