Hydrochloric Acid → 3-(Pyridin-3-yl)cyclohex-2-en-1-one

HRID 655168Notes

Reaction equation

HRID 655168 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.C([O:15][C:16]1[CH2:21][CH2:20][CH2:19][C:18](=O)[CH:17]=1)C.Cl>CCOCC>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:18]2[CH2:19][CH2:20][CH2:21][C:16](=[O:15])[CH:17]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 122863-BromopyridineHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 178418339Butyllithium

Product 1

HCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-oneYield 66.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of n-BuLi (1.54 M in Hexane, 145 mL. 224 mmol) in Et2O (600 ml) was added dropwise 3-Bromopyridine (22.0 mL, 224 mmol) at −75˜−68° C., and stirred for 20 min. To a reaction mixture was added dropwise 3-ethoxy-2-cyclohexenone (25.0 mL, 187 mmol) at −75˜−69° C., and stirred at room temperature for 1 h. The reaction mixture was acidified with 2M HCl (300 mL), and aqueous layer was washed with AcOEt. 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=1/2) to yield 3-(3-pyridyl)-2-cyclohexen-1-one (21.5 g, 66%) as yellow powder.

Workup

  1. stirringstirred at room temperature for 1 h
  2. washwas washed with AcOEt
  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=1/2)

Sources & evidence

ORD record
ord-ebad726ebe5549f7a3b15924772bd3dd
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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