Hydrogen chloride-ethyl acetate → 4-(2-Hydroxyethoxy)-6-methylpyridin-3-ol

HRID 1038591Notes

Reaction equation

HRID 1038591 reaction equation
COC[O:4][C:5]1[C:6]([O:12][CH2:13][CH2:14][OH:15])=[CH:7][C:8]([CH3:11])=[N:9][CH:10]=1.Cl.C(OCC)(=O)C>C(OCC)(=O)C>[OH:15][CH2:14][CH2:13][O:12][C:6]1[CH:7]=[C:8]([CH3:11])[N:9]=[CH:10][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 665986772-(5-(Methoxymethoxy)-2-methylpyridin-4-yloxy)ethanol

Product 1

HCID 665990334-(2-Hydroxyethoxy)-6-methylpyridin-3-olYield 168.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(5-(Methoxymethoxy)-2-methylpyridin-4-yloxy)ethanol (900 mg, 4.22 mmol) was dissolved in ethyl acetate (10 mL), added 4N hydrochloric acid-ethyl acetate solution (10 mL), and the mixture was stirred at room temperature for 5 hours. After the reaction has terminated, under ice-cold conditions, a 4N aqueous solution of sodium hydroxide was used to adjust the reaction solution to pH=8. The reaction solution was concentrated in vacuo. The obtained residue was washed with chloroform/methanol, dried, and as a crude product, 4-(2-hydroxyethoxy)-6-methylpyridin-3-ol (1.2 g) was obtained as a white solid.

Workup

  1. customAfter the reaction has terminated, under ice-cold conditions
  2. concentrationThe reaction solution was concentrated in vacuo
  3. washThe obtained residue was washed with chloroform/methanol
  4. customdried

Sources & evidence

ORD record
ord-7c7aa91cd96b43d8bb3ca03f61598f8f
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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