Water → Diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate

HRID 1267475노트

반응식

HRID 1267475 반응식
[H-].[Na+].[CH2:3]([CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9].I[CH2:22][CH2:23][CH2:24][C:25]([F:37])([F:36])[C:26]([F:35])([F:34])[C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29].O>O1CCCC1>[CH2:3]([C:10]([CH2:22][CH2:23][CH2:24][C:25]([F:36])([F:37])[C:26]([F:34])([F:35])[C:27]([F:32])([F:33])[C:28]([F:29])([F:31])[F:30])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 120167744,4,5,5,6,6,7,7,7-Nonafluoroheptyl iodideHCID 18546274Diethyl 2-(6-heptenyl)malonate

생성물 1

HCID 12015792Diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate수율 101.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

60% sodium hydride (0.54 g, 13.5 mmol) was added to a solution of diethyl 2-(6-heptenyl)malonate (3.0 g, 11.7 mmol) in tetrahydrofuran (30 ml) followed by stirring for 30 minutes at room temperature. 1-Iodo-4,4,5,5,6,6,7,7,7-nonafluoroheptane (5.45 g, 14.04 mmol) was added to the mixture followed by stirring for 12 hours at room temperature. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/25) to give diethyl 2-(6-heptenyl)-2-(4,4,5,5,6,6,7,7,7-nonafluoroheptyl)malonate (6.14 g, quantitative) as a colorless oil.

후처리

  1. stirringby stirring for 12 hours at room temperature
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter distilling off the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/25)

출처 및 근거

ORD 기록
ord-0726abbee2f64c1fbc4ef560641d4557
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552069B1

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