Water → 4-(Pyridin-3-yl)cyclohexan-1-one

HRID 655158Notes

Reaction equation

HRID 655158 reaction equation
O.C1O[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4]C1.C([O-])(O)=O.[Na+].[OH-].[Na+]>C(C(O)=O)(F)(F)F>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 578925504-(3-Pyridyl)cyclohexanone ethylene acetal

Product 1

HCID 200349074-(Pyridin-3-yl)cyclohexan-1-oneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Water (1 mL) was added to a cod solution of 4-(3-pyridyl)cyclohexanone ethylene acetal (4.79 g, 21.9 mmol) in CF3CO2H (20 mL). After stirring room temperature for 6 h, the reaction mixture was added dropwise to sat. NaHCO3. aq. The resulting mixture was adjusted to pH 8 with 2M NaOH aq. and extracted with CH2Cl2, After drying and consentration, the crude product was purified by column chromatography (Hexane/EtOAc=1/1→0/1) to yield 4-(3-pyridyl)cyclohexanone (3.23 g, 84%) as a colorless powder.

Workup

  1. extractionextracted with CH2Cl2
  2. customAfter drying
  3. customconsentration, the crude product was purified by column chromatography (Hexane/EtOAc=1/1→0/1)

Sources & evidence

ORD record
ord-5e03fba41efe444c90de65b7aea4ef74
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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