Allyl bromide → (3-Allyloxy-pyridin-2-yl)-methanol

HRID 1761403Notes

Reaction equation

HRID 1761403 reaction equation
C[O-].[Na+].[Na].[OH:5][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1.[CH2:14](Br)[CH:15]=[CH2:16]>CS(C)=O.CO>[CH2:16]([O:5][C:6]1[C:7]([CH2:12][OH:13])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH:15]=[CH2:14]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 841693-Hydroxypyridine-2-methanolHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 14598977(3-Allyloxy-pyridin-2-yl)-methanol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent2×

Procedure

To a sodium methoxide, methanol mixture made from 1.43 g (62 mmole) sodium metal and 100 ml methanol was added 5.9 g (31 mmole) 3-hydroxy-2-hydroxymethylpyridine and the methanol removed in vacuo. The resulting residue was dissolved in 80 ml dimethylsulfoxide (DMSO) and 3.0 ml (34.7 mmole) allyl bromide in 20 ml DMSO was added over 20 minutes at room temperature. The mixture was stirred for two hours, the DMSO distilled in vacuo and the residue partitioned betwen chloroform/water. The aqueous phase was adjusted to pH 7.5 and extracted three times with chloroform. The combined organic layers were washed with water, brine, dried (Na2SO4) and concentrated to give 3.48 g (68%) of the desired ether.

Workup

  1. customthe methanol removed in vacuo
  2. dissolutionThe resulting residue was dissolved in 80 ml dimethylsulfoxide (DMSO)
  3. distillationthe DMSO distilled in vacuo
  4. customthe residue partitioned betwen chloroform/water
  5. extractionextracted three times with chloroform
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give 3.48 g (68%) of the desired ether

Sources & evidence

ORD record
ord-b87c27a467a54733b824435931f70167
Source dataset
uspto-grants-1989_05
Patent number
US04826833

Reaction notes

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