1-(6-Chloropyridin-3-yl)butan-1-ol → 1-(6-Chloropyridin-3-yl)butan-1-one

HRID 1892717Notes

Reaction equation

HRID 1892717 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 804616451-(6-Chloropyridin-3-yl)butan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 454801741-(6-Chloropyridin-3-yl)butan-1-oneYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(6-chloropyridin-3-yl)butan-1-ol (210 mg, 1.13 mmol) in 10 mL dichloromethane was added 2 g of silica gel, followed by pyridinium chlorochromate (488 mg, 2.26 mmol) The mixture was stirred at room temperature 5 h. The mixture was filtered through a plug of silica gel, eluting with 100 mL dichloromethane. The eluent was concentrated to give 1-(6-chloropyridin-3-yl)butan-1-one (210 mg). 1H NMR (400 MHz, CDCl3) δ 8.88-8.96 (m, 1H), 8.14-8.20 (m, 1H), 7.42 (d, J=8.4 Hz, 1H), 2.92 (t, J=7.2 Hz, 2H), 1.70-1.82 (m, 2H), 0.99 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through a plug of silica gel
  2. washeluting with 100 mL dichloromethane
  3. concentrationThe eluent was concentrated

Sources & evidence

ORD record
ord-fe9566131b214aadab3a5808834a7ff7
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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