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

HRID 2185163ノート

反応式

HRID 2185163 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 135280095-(1-Cyclopentenyl)pentan-2-one収率 72.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 15413tert-Butyl methyl ether溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-74036c35ea5443259811297d2d5a8373
出典データセット
uspto-grants-2002_06
特許番号
US06399811B1

反応ノート

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