p-Toluenesulfonic acid → 3-Bromo-4-cyclopent-1-enyl-pyridine

HRID 523590ノート

反応式

HRID 523590 の反応式
CC1C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1(O)[CH2:23][CH2:22][CH2:21][CH2:20]1.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH2:23][CH2:22][CH2:21][CH:20]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 70982889HCID 70982889、化合物

生成物 1

HCID 709821203-Bromo-4-cyclopent-1-enyl-pyridine収率 73%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

反応条件

温度
120 °C

実験手順

PTSA (819 mg, 4.315 mmol) was added portionwise to a stirred mixture of 1-(3-bromo-pyridin-4-yl)-cyclopentanol (I-34a: 520 mg, 2.15 mmol) in 25 mL of toluene. The resulting mixture was heated to reflux at 120° C. for 4 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was concentrated, basified with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated to afford the crude product. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 350 mg of the product (73% yield).

後処理

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (8% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-88d3e6018d424e7d9c6a9972636fa12b
出典データセット
uspto-grants-2016_05
特許番号
US09339501B2

反応ノート

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