Water → 2-(4,4-Ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl ester

HRID 1607403

반응식

HRID 1607403 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[CH2:25]1[CH2:39][O:38][C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([CH2:28][CH2:29][CH2:30]Br)[O:26]1.O>COCCOC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:30][CH2:29][CH2:28][C:27]1([O:26][CH2:25][CH2:39][O:38]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH3:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 9972002Diethyl (1-naphthyl)methylmalonateHCID 147642024,4-Ethylenedioxy-4-phenylbutyl bromide

생성물 1

HCID 538686682-(4,4-Ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl ester수율 66.8%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution of 1.1 g of 2-(1-naphthylmethyl)malonic acid diethyl ester in 20 ml of dry 1,2-dimethoxyethane was added 0.22 g of a 50% sodium hydride (suspension in oil) under cooling, the mixture was stirred for 1 hour. To the reaction mixture was added 1.0 g of 4,4-ethylenedioxy-4-phenylbutyl bromide obtained, the mixture was heated under reflux for 17 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 1.2 g of 2-(4,4-ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl ester.

후처리

  1. temperatureunder cooling
  2. customobtained
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 17 hours
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with diethyl ether
  7. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)

출처 및 근거

ORD 기록
ord-525f7d7838bc4d63939565c0b2657e29
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04863904

연결된 노트

불러오는 중…