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

HRID 909374Notes

Reaction equation

HRID 909374 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-40f3f697a8e94d8caa2ee98c60b08a95
Source dataset
uspto-grants-2011_09
Patent number
US08017788B2

Reaction notes

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