Sodium hydride → Ethyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]-2-propenoate

HRID 366349노트

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HRID 366349 반응식
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH2:7][O:8][CH2:9][CH2:10]P(OCC)(OCC)=O)[CH3:4].[CH2:20]([O:22][CH:23]([O:34][CH2:35][CH3:36])[CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[CH3:21]>C1COCC1>[CH2:9]([O:8][C:7](=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH:23]([O:34][CH2:35][CH3:36])[O:22][CH2:20][CH3:21])=[CH:27][CH:28]=1)[C:6]([O:5][CH2:3][CH3:4])=[O:19])[CH3:10]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 15729465Ethyl (diethoxyphosphoryl)ethoxyacetateHCID 187608894-(2,2-Diethoxyethoxy)benzaldehyde

생성물 1

HCID 54302220Ethyl 2-ethoxy-3-[4-[(2,2-diethoxy)ethoxy]phenyl]-2-propenoate수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

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온도
15 °C

실험 절차

To a stirred suspension of sodium hydride (756 mg, 32 mmol, 95%) in dry THF (60 mL) was added a solution of ethyl(diethylphosphono)ethoxyacetate (6.20 g, 23.1 mmol) in THF (20 mL) at 0-5° C. dropwise and stirred for 30 min at 5-25° C. To the reaction mixture was added a solution of 4-[(2,2-diethoxy)ethoxy]benzaldehyde (5.0 g, 21.0 mmol) in THF (10 mL) at 25° C. and stirred further for 30 min. After completion of the reaction (TLC monitored), THF was removed and the resultant residue was diluted with water (100 mL) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated to yield the title compound (6.5 g, 88%) as a mixture of E/Z isomers.

후처리

  1. stirringstirred further for 30 min
  2. customwas removed
  3. additionthe resultant residue was diluted with water (100 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-aa2569c04d6441dcb77318a1e9c77f29
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130214

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