Methyl iodide → 2-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester

HRID 81764ノート

反応式

HRID 81764 の反応式
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17])[CH3:2].[H-].[Na+].[CH:22]([O:24][CH2:25]C)=O.IC>COCCOC>[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17])=[CH:22][O:24][CH3:25])[CH3:2]

参加物

6

反応物 4

HCID 6328Methyl iodideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 59598614(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester

生成物 1

HCID 670534762-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester収率 23.2%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

To a solution of (2-isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester (4.42 g, 16.6 mmol) in anhydrous 1,2-dimethoxy ethane (60 ml) was added sodium hydride (60% in mineral oil, 3.5 g, 87.5 mmol) at room temperature. After 5 minutes of stirring, ethyl formate (40 ml, 495 mmol) was added. The mixture was heated at 85° C. for 7 hours. After cooling to room temperature, iodomethane was added and stirring was continued overnight. Solvent was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified with silica gel chromatography (10% to 30% ethyl acetate in hexane) to yield 2-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester as a pale yellow oil (1.19 g, 23%).

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringstirring
  3. waitwas continued overnight
  4. concentrationSolvent was concentrated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. washThe organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removal
  9. customof drying agent
  10. concentrationthe organic solution was concentrated under reduced pressure
  11. customThe residue was purified with silica gel chromatography (10% to 30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-c1a6596161c846c0a6de2620446a2c2b
出典データセット
uspto-grants-2014_09
特許番号
US08846705B2

反応ノート

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