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

HRID 523590노트

반응식

HRID 523590 반응식
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

참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 70982889HCID 70982889, 화합물

생성물 1

HCID 709821203-Bromo-4-cyclopent-1-enyl-pyridine수율 73%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-88d3e6018d424e7d9c6a9972636fa12b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09339501B2

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