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

HRID 1677264노트

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HRID 1677264 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e747eba6f2c84aa38915692af01169ca
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008313B2

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