Allyl Alcohol → HCID 22020954, compound

HRID 1793331Notes

Reaction equation

HRID 1793331 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[CH2:8]([OH:11])[CH:9]=[CH2:10].[H-].[Na+]>O>[CH2:8]([O:11][C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1)[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 783445-Bromopyrimidine

Product 1

HCID 22020954HCID 22020954, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Bromo-pyrimidine (0.063 mol) was slowly added to 2-propen-1-ol (4.03 mol) at 0° C. and this mixture was stirred at room temperature for 1 hour. Then NaH 60% (0.126 mol) was added and the reaction mixture was stirred and refluxed for 48 hours. Water was added and the mixture was extracted with ethyl acetate. The separated organic layer was dried, filtered and the solvent was evaporated. The residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 50/50). The desired fractions were collected and the solvent was evaporated, yielding 2.3 g of 5-(2-propenyloxy)-pyrimidine (intermediate 48).

Workup

  1. stirringthe reaction mixture was stirred
  2. temperaturerefluxed for 48 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by short open column chromatography over silica gel (eluent: hexane/ethyl acetate 50/50)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-163dcc41d9d344648276574598d51bb8
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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