Formaldehyde → 2-(5-(1-(Methoxymethoxy)ethyl)pyridin-2-yl)ethanol

HRID 1756630Notes

Reaction equation

HRID 1756630 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[CH3:6].[CH2:14]=[O:15]>>[CH3:1][O:2][CH2:3][O:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][OH:15])=[N:11][CH:12]=1)[CH3:6]

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 107025455-[1-(Methoxymethoxy)ethyl]-2-methylpyridine

Product 1

HCID 106085532-(5-(1-(Methoxymethoxy)ethyl)pyridin-2-yl)ethanolYield 32%

Procedure

The mixture of 5-(1-methoxymethoxyethyl)-2-methylpyridine (21.0 g) and formalin (37% aq. HCHO, 14.1 g) was heated at 150° to 160° C. for 8 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure and then the residue was subjected to silica gel column chromatography. A fraction eluted with chloroform-methanol (25:1, v/v) gave 2-[5-(1-methoxymethoxyethyl)-2-pyridyl]ethanol (7.8 g, yield: 32%) as oil.

Workup

  1. temperaturewas heated at 150° to 160° C. for 8 hours in a sealed tube
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washA fraction eluted with chloroform-methanol (25:1

Sources & evidence

ORD record
ord-7507577fcf86424d8bf3fb0711558800
Source dataset
uspto-grants-1995_08
Patent number
US05441971

Reaction notes

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