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

HRID 655136ノート

反応式

HRID 655136 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 392355473-(2-Pyridyl)-2-cyclopenten-1-one収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c46e860a09db44bf83a44588dea15a21
出典データセット
uspto-grants-2011_12
特許番号
US08071591B2

反応ノート

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