Ethanol → Ethyl 3-hydroxy-5-methoxypicolinate

HRID 869635ノート

反応式

HRID 869635 の反応式
[OH:1][C:2]1[C:3]([C:10]([OH:12])=[O:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH2:13](O)[CH3:14]>S(=O)(=O)(O)O.C(OCC)(=O)C>[OH:1][C:2]1[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:4][CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

参加物

5

反応物 2

HCID 702EthanolHCID 215430083-Hydroxy-5-methoxypicolinic acid

生成物 1

HCID 66962131Ethyl 3-hydroxy-5-methoxypicolinate収率 76%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 8857Ethyl Acetate溶媒

実験手順

3-hydroxy-5-methoxypicolinic acid (200 mg, 1.18 mmol) was dissolved in ethanol (10 mL). To the mixture was added one drop of sulfuric acid. The mixture was refluxed with stirring for 3 days. After cooling to room temperature, the mixture was concentrated in vacuo to afford an oil. The residual oil was dissolved in ethyl acetate and washed with aq. sodium bicarbonate and brine. The extract was dried over sodium sulfate and concentrated in vacuo to afford an oil. The residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:3 to 1:1) to afford 178 mg (76%) of the title compound as a white solid.

後処理

  1. temperatureThe mixture was refluxed
  2. concentrationthe mixture was concentrated in vacuo
  3. customto afford an oil
  4. washwashed with aq. sodium bicarbonate and brine
  5. dry with materialThe extract was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto afford an oil
  8. customThe residual oil was purified by silica gel column chromatography (ethyl acetate/hexane 1:3 to 1:1)

出典と根拠

ORDレコード
ord-f85fc349153d4aadaf47d4061d5f92e1
出典データセット
uspto-grants-2015_03
特許番号
US08969383B2

反応ノート

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