p-Toluenesulfonic acid → 5-(1-Cyclopentenyl)pentan-2-one

HRID 2185163노트

반응식

HRID 2185163 반응식
[C:1]1(=[CH:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CC(OC)(C)C>[C:1]1([CH2:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH:2]=1

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 135280135-Cyclopentylidenepentan-2-one

생성물 1

HCID 135280095-(1-Cyclopentenyl)pentan-2-one수율 72.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5-cyclopentylidene-2-pentanone (9.92 g; 65 mmol) and p-TsOH (100 mg; 0.53 mmol) in toluene (150 ml) was heated at 90° C. for 8 hours, then cooled down to room temperature, diluted with MTBE (100 ml), washed with saturated NaHCO3 (50 ml), H2O (50 ml), brine (50 ml), dried over MgSO4 and concentrated in vacuo. Distillation under reduced pressure (48° C./0.065 torr) yielded 7.13 g of 5-(cyclopent-1-enyl)-2-pentanone (purity about 80%), which was further purified by flash chromatography to give 6.1 g (61% yield) of a 89% pure product containing 11% of 5-cyclopentylidene-2-pentanone.

후처리

  1. temperaturecooled down to room temperature
  2. washwashed with saturated NaHCO3 (50 ml), H2O (50 ml), brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. distillationDistillation under reduced pressure (48° C./0.065 torr)

출처 및 근거

ORD 기록
ord-74036c35ea5443259811297d2d5a8373
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399811B1

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