Water → Diethyl 2-(6-heptenyl)malonate

HRID 1267751노트

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HRID 1267751 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].I[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[CH2:21].O>O1CCCC1>[CH2:21]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=[CH2:15]

참가 물질

6

반응물 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 106328827-Iodohept-1-ene

생성물 1

HCID 18546274Diethyl 2-(6-heptenyl)malonate수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60%, 5.78 g, 144.59 mmol) was added to anhydrous tetrahydrofuran (250 ml) and cooled to 0° C. To this mixture, diethyl malonate (25.09 g, 156.64 mmol) was slowly added dropwise, followed by stirring for 1 hour at room temperature. 7-Iodo-1-heptene (27 g, 120.49 mmol) dissolved in anhydrous tetrahydrofuran (50 ml) was then slowly added dropwise to the mixture, followed by stirring for 12 hours at room temperature. Water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were 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=1/40) to give diethyl 2-(6-heptenyl)malonate (25.8 g, Yield 84%).

후처리

  1. additionwas then slowly added dropwise to the mixture
  2. stirringby stirring for 12 hours at room temperature
  3. extractionwas then extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/40)

출처 및 근거

ORD 기록
ord-4e6a7302a653429c8cb588779f798d95
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06552068B1

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