Hydrochloric Acid → 3-(2-Pyridyl)-2-cyclopenten-1-one

HRID 655136노트

반응식

HRID 655136 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.C([O:15][C:16]1[CH2:20][CH2:19][C:18](=O)[CH:17]=1)C.Cl>C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH2:19][CH2:20][C:16](=[O:15])[CH:17]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 897773-Ethoxycyclopent-2-en-1-oneHCID 178418339Butyllithium

생성물 1

HCID 392355473-(2-Pyridyl)-2-cyclopenten-1-one수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2-Bromopyridine (5.00 g, 31.6 mmol) in THF (30 ml) was added dropwise n-BuLi (2.55 M in Hexane, 12.5 mL. 31.9 mmol) at −78° C., and stirred for 10 min. To a reaction mixture was added dropwise 3-ethoxy-2-cyclopentenone (2.00 g, 15.9 mmol) in THF (10 mL) at −78° C., and stirred at 0° C. for 2 h. The reaction mixture was acidified with 2M HCl (10 mL), and aqueous layer was washed with EtOAc. The aqueous layer was basified with 1M NaOH aq., and then extracted with CH2Cl2. The organic layer was washed with brine, and dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=1/3) to yield 3-(2-pyridyl)-2-cyclopenten-1-one (1.57 g, 58%) as brown solid.

후처리

  1. stirringstirred at 0° C. for 2 h
  2. washwas washed with EtOAc
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhyd Na2SO4
  6. customfollowed by the removal of solvent
  7. customThe crude product was purified by column chromatography (Hexane/EtOAc=1/3)

출처 및 근거

ORD 기록
ord-c46e860a09db44bf83a44588dea15a21
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071591B2

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