Allyl Alcohol → HCID 22020921, compound

HRID 1793308Notes

Reaction equation

HRID 1793308 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[H-].[Na+].[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1Cl>COCCOC>[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[O:4][CH2:1][CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 220209744-Chloro-3-(methoxymethoxy)pyridine

Product 1

HCID 22020921HCID 22020921, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Under nitrogen atmosphere. 2-propen-1-ol (0.002 mol) was added dropwise to a stirred mixture of NaH 60% (0.002 mol) in DME (5ml). The mixture was stirred at room temperature for 15 minutes. A solution of 3-(methoxymethoxy)-4-chloropyridine (0.0017 mol) in DME (5 ml) was added dropwise. The resulting reaction mixture was stirred at reflux overnight. The mixture was washed with water and extracted with ethyl acetate. The organic layer was dried, filtered and evaporated till dryness. The residue was purified by open column chromatography (eluent: hexane/ethyl acetate 3/2; CH2Cl2/2-propanone 90/10; CH2Cl2/MeOH 96/4). The product fractions were collected and the solvent was evaporated, yielding 0.18 g of 3-(methoxymethoxy)-4-(2-propenyloxy)pyridine (intermediate 7).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred
  3. temperatureat reflux overnight
  4. washThe mixture was washed with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated till dryness
  9. customThe residue was purified by open column chromatography (eluent: hexane/ethyl acetate 3/2; CH2Cl2/2-propanone 90/10; CH2Cl2/MeOH 96/4)
  10. customThe product fractions were collected
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-55ae6d3dbf894db8b54952ca5af88cf3
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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