Methanol → (3-Allyloxy-pyridin-2-yl)-methanol

HRID 449847Notes

Reaction equation

HRID 449847 reaction equation
Cl.[OH:2][C:3]1[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=1.CO.C[O-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18]>O>[CH2:18]([O:2][C:3]1[C:4]([CH2:9][OH:10])=[N:5][CH:6]=[CH:7][CH:8]=1)[CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 887Methanol2×HCID 7841Allyl bromideHCID 30841853-Hydroxy-2-(hydroxymethyl)pyridine hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 14598977(3-Allyloxy-pyridin-2-yl)-methanolYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

Hydroxy-2-(hydroxymethyl)pyridine hydrochloride (50 g, 339.6 mmol) and methanol (250 mL) are combined under nitrogen and cooled to 22° C. To the vigorously stirred mixture is added 4.5 M sodium methoxide in MeOH (170.8 mL, 747.2 mmol). The mixture is stirred at room temperature for 2 h and then the solvent is evaporated. The resulting material is dissolved in DMSO (250 mL), allyl bromide (41 g, 339.6 mmoles) is added, and the mixture stirred for 18 h at room temperature. The reaction mixture is added to water (800 mL) and extracted with methylene chloride (3×80 mL). The organic portions are combined and dried over sodium sulfate, filtered, and the solvent evaporated to afford the title compound (34.4 g, 62%). LC-ES/MS m/z 166.1 [M+H]+.

Workup

  1. customthe solvent is evaporated
  2. dissolutionThe resulting material is dissolved in DMSO (250 mL)
  3. stirringthe mixture stirred for 18 h at room temperature
  4. extractionextracted with methylene chloride (3×80 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-3c0e8652eb3f4c2bafbc23a74e5f7fc7
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

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