Diisopropylamine → Ethyl (Z)-3-(3,4-dimethoxyphenyl)-2-(3-pyridyl)-2-propenoate

HRID 260880

반응식

HRID 260880 반응식
C([Li])CCC.C(NC(C)C)(C)C.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:14]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH:30]=O>O1CCCC1.O>[CH3:25][O:26][C:27]1[CH:28]=[C:29](/[CH:30]=[C:19](/[C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)\[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 8419VeratraldehydeHCID 96490Ethyl 3-pyridylacetateHCID 178418339Butyllithium

생성물 1

HCID 86749581Ethyl (Z)-3-(3,4-dimethoxyphenyl)-2-(3-pyridyl)-2-propenoate수율 37%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

n-Butyllithium (1.6M hexane solution, 99.2 ml) was dropped into a solution of diisopropylamine (23.4 ml, 166.6 mmol) in tetrahydrofuran (320 ml). The obtained mixture was stirred at 0° C. for 30 minutes. A solution of ethyl 3-pyridylacetate (24.0 ml, 158.9 mmol) in tetrahydrofuran (20 ml) was dropped into the resulting mixture at -70° C. and the obtained mixture was stirred at 0° C. for 15 minutes. A solution of 3,4-dimethoxybenzaldehyde (27.6 g, 166.0 mmol) in tetrahydrofuran (100 ml) was dropped into the mixture at 0° C. The obtained mixture was stirred at room temperature overnight, followed by the addition of water. The obtained mixture was extracted with ether. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate and concentrated. The oily residue was purified by flash column chromatography (ethyl acetate/hexane=3:2) to give the title compound as a pale yellow oil (18.19 g, yield: 37%).

후처리

  1. stirringthe obtained mixture was stirred at 0° C. for 15 minutes
  2. stirringThe obtained mixture was stirred at room temperature overnight
  3. extractionThe obtained mixture was extracted with ether
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe oily residue was purified by flash column chromatography (ethyl acetate/hexane=3:2)

출처 및 근거

ORD 기록
ord-b306a320788f41a5b4c77440dbb3afa3
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530118

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