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Sodium ethoxide → Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoate

HRID 2268483
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HRID 2268483 반응식
[O-:1][CH2:2][CH3:3].[Na+].[C:5]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:6][C:7]([O-:9])=O.I[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1>C(O)C.O>[CH2:2]([O:1][C:7]([CH:6]([CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][CH:20]=1)[C:5]([O:11][CH2:12][CH3:13])=[O:10])=[O:9])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 2723922Sodium ethoxideHCID 3595298Propanedioic acid, monoethyl esterHCID 18348598Ethyl 4-(3-iodopropoxy)benzoate

생성물 1

HCID 18348516Ethyl 2-ethoxycarbonyl-5-(4-ethoxycarbonylphenoxy)pentanoate수율 47.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962
Water
용매

실험 절차

To a solution of sodium ethoxide (90%, 6.79 g) in ethanol (250 ml) was dropwise added ethyl malonate (12.0 g) with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 30 min and ethyl 4-(3-iodopropoxy)benzoate (25.0 g) was dropwise added with cooling with ice. The reaction mixture was allowed to warm to room temperature and stirred for 12 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to yield the entitled compound (13.0 g) as an oil.

후처리

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. temperatureto warm to room temperature
  4. stirringstirred for 12 hr
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated aqueous sodium chloride
  7. customdried
  8. customThe solvent was removed in vacuo
  9. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-cfa28ac0c36c4948a5eb142ec90c6d39
출처 데이터셋
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06326369B1

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