2,3-Dimethoxy-4-(1'-hydroxypropyl)pyridine → 1-(2,3-Dimethoxy-pyridin-4-yl)-propan-1-one

HRID 2246190Notes

Reaction equation

HRID 2246190 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([CH:22]([OH:25])[CH2:23][CH3:24])[CH:17]=[CH:16][N:15]=1>ClCCl>[CH3:12][O:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([C:22](=[O:25])[CH2:23][CH3:24])[CH:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 592179372,3-Dimethoxy-4-(1'-hydroxypropyl)pyridineHCID 178418287HCID 178418287, compound

Product 1

HCID 592179421-(2,3-Dimethoxy-pyridin-4-yl)-propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Celite (27 g, oven dried) and pyridinium chlorochromate (26.46 g; 12.27 mmol) were added to a solution of 2,3-dimethoxy-4-(1′-hydroxypropyl)pyridine (4) (18.6 g; 94.4 mmol) in anhydrous dichloromethane (300 mL). The resultant mixture was stirred at room temperature for 16 hours. The mixture was then filtered through a pad of Celite and silica gel. Concentration generated 13.8 g of the crude 1-(2,3-dimethoxy-pyridin-4-yl)-propan-1-one (5) product which was utilized in the subsequent synthesis step without further purification.

Workup

  1. filtrationThe mixture was then filtered through a pad of Celite and silica gel
  2. concentrationConcentration
  3. customwas utilized in the subsequent synthesis step without further purification

Sources & evidence

ORD record
ord-65462254310b44aca0660e7e2ca26048
Source dataset
uspto-grants-2010_03
Patent number
US07687487B2

Reaction notes

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