p-Toluenesulfonic acid → Spiro(4.5)dec-6-ene-8-one

HRID 2218796노트

반응식

HRID 2218796 반응식
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]([C:10]([CH3:12])=[O:11])=[CH2:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:2]1[C:1]2([CH2:6][CH2:12][C:10](=[O:11])[CH:8]=[CH:9]2)[CH2:5][CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 6570Methyl vinyl ketoneHCID 70106Cyclopentanecarbaldehyde

생성물 1

HCID 139772Spiro(4.5)dec-6-ene-8-one수율 39.9%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

To a solution of cyclopentanecarbaldehyde (10 g, 100 mmol) in toluene (100 mL) were added methyl vinyl ketone (7.8 g, 110 mmol) and p-toluenesulfonic acid (1.9 g, 10 mmol), and the mixture was stirred at 120° C. for 3 hours, using a Dean-Stark apparatus to remove water. The reaction mixture was air-cooled to room temperature, then saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 6.0 g of the title compound as a red oil.

후처리

  1. customto remove water
  2. temperatureThe reaction mixture was air-cooled to room temperature
  3. additionsaturated aqueous sodium hydrogencarbonate was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e4e2f24740254a53bd0d14be4d69979e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07410971B2

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