Potassium Carbonate → {3-[2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}methanol

HRID 1765083Notes

Reaction equation

HRID 1765083 reaction equation
Cl.[OH:2][CH2:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1>C(#N)C>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:21]1[O:20][CH2:19][CH2:18][O:10][C:9]1[C:4]([CH2:3][OH:2])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 30841853-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride

Product 1

HCID 21106673{3-[2-(Tetrahydro-2H-pyran-2-yloxy)ethoxy]pyridin-2-yl}methanolYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 85% pure 2-(hydroxymethyl)pyridin-3-ol hydrochloride (24.9 g, 130 mmol) and potassium carbonate (60 g, 434 mmol) in acetonitrile (200 mL) was heated at reflux for 15 minutes after which 2-(2-bromoethoxy)tetrahydro-2H-pyran (32.9 g, 160 mmol) was added in one portion and the heating was continued overnight. Solids were filtered off and the solvent was removed under reduced pressure and the resulting oil was chromatographed on a column of silica (100 mm, i.d.=60 mm) with CHCl3 as eluent followed by CHCl3/MeOH/NH4OH (95:5:0.2) to give 28.4 g (93%) of the title compound as a light brown oil. HRMS m/z calcd for C13H19NO4 (M)+ 253.1314. found 253.1326.

Workup

  1. temperaturewas heated
  2. additionwas added in one portion
  3. filtrationSolids were filtered off
  4. customthe solvent was removed under reduced pressure
  5. customthe resulting oil was chromatographed on a column of silica (100 mm, i.d.=60 mm) with CHCl3 as eluent

Sources & evidence

ORD record
ord-96a5a802305e481688ff41bad863dd5b
Source dataset
uspto-grants-2007_06
Patent number
US07226925B2

Reaction notes

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