Hydrochloric Acid → 3-(6-Chloropyridin-3-yl)cyclopentanone

HRID 1927203Notes

Reaction equation

HRID 1927203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][C:10]([O:13][Si](C)(C)C)=[CH:9]2)=[CH:4][N:3]=1.Cl>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 592659422-Chloro-5-(3-trimethylsilanyloxycyclopent-2-enyl)pyridine

Product 1

HCID 592659583-(6-Chloropyridin-3-yl)cyclopentanoneYield 37.2%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Chloro-5-(3-trimethylsilanyloxycyclopent-2-enyl)pyridine (0.58 g, 2.2 mmol) was dissolved in THF (10 mL) in a 100 mL round bottom flask and treated with 1N HCl (2 mL) with stirring at room temperature. After 1 h, the mixture was diluted with EtOAc and sat. NaHCO3 and the layers separated. The aqueous phase was extracted with EtOAc and the combined organic layers dried (Na2SO4), filtered, concentrated, and purified by flash silica gel chromatography (hexanes: EtOAc/2:1) to give 3-(6-chloropyridin-3-yl)cyclopentanone (0.16 g, 37%) as a dark oil: LC/MS (ESI) m/z 195, 1H NMR (300 MHz, CDCl3) δ 8.31 (d, 1H, J=2.7 Hz), 7.54 (dd, 1H, J=8.4, 2.7 Hz), 7.31 (d, 1H, J=8.4 Hz), 3.43 (m, 1H), 2.70 (m, 1H), 2.56-2.22 (m, 4H), 1.97 (m, 1H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe combined organic layers dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash silica gel chromatography (hexanes: EtOAc/2:1)

Sources & evidence

ORD record
ord-c96562561de64728a8447da5c4425f37
Source dataset
uspto-grants-2012_05
Patent number
US08183268B2

Reaction notes

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