Sodium Hydroxide → HCID 178430566, compound

HRID 2106001Notes

Reaction equation

HRID 2106001 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10][OH:11])[C:4]=1[CH3:12].[Cl-].[Li+].[OH-].[Na+]>CN(C)C=O>[OH:11][CH2:10][C:5]1[C:4]([CH3:12])=[C:3]([OH:2])[C:8]([CH3:9])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

Product 1

HCID 178430566HCID 178430566, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-methoxy-3,5-dimethylpyridin-2-yl)methanol (1.0 g) and anhydrous lithium chloride (0.76 mg) in dimethylformamide (10 mL) was heated at reflux for 43 hours. Sodium hydroxide solution (10% w/v, 30 mL) was then added and the resulting solution was extracted twice with diethyl ether. The aqueous phase was neutralized with 1N HCl (21 mL) and the volatiles were removed in vacuo. The resulting solid was purified by column chromatography with silica gel (eluted with 10% methanol-methylene chloride). Product-rich fractions were combined, concentrated in vacuo, and triturated with chloroform-acetonitrile (4:1) to afford the product, 2-hydroxymethyl-3,5-dimethylpyridin-4-ol, as a white solid (0.78 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 43 hours
  3. extractionthe resulting solution was extracted twice with diethyl ether
  4. customthe volatiles were removed in vacuo
  5. customThe resulting solid was purified by column chromatography with silica gel (eluted with 10% methanol-methylene chloride)
  6. concentrationconcentrated in vacuo
  7. customtriturated with chloroform-acetonitrile (4:1)

Sources & evidence

ORD record
ord-9e654e23e06f4f2a87c8b50fc9214286
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

Loading…