Water → HCID 22105558, compound

HRID 1455962Notes

Reaction equation

HRID 1455962 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH3:15])=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Se](=O)=[O:17].O>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[O:17])=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 22105561HCID 22105561, compound

Product 1

HCID 22105558HCID 22105558, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Benzyloxy-3-methylpyrazine (600 mg) was dissolved in 1,4-dioxane (12 mL), selenium dioxide (1 g) and water added (one drop) and the mixture heated at reflux for seventeen hours. The reaction mixture was allowed to cool to ambient temperature, filtered and the solvents removed. The residue was dissolved in water (30 mL), neutralised with aqueous sodium hydrogen carbonate solution (10%) and extracted with dichloromethane (3×40 mL), the organic phase was dried (MgSO4). After removal of the solvents the oil was purified by MPLC (15%ethyl acetate, hexane, silica) to give 2-benzyloxypyrazine-3-aldehyde (460 mg, mp 69.4° C.).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for seventeen hours
  3. filtrationfiltered
  4. customthe solvents removed
  5. dissolutionThe residue was dissolved in water (30 mL)
  6. extractionextracted with dichloromethane (3×40 mL)
  7. dry with materialthe organic phase was dried (MgSO4)
  8. customAfter removal of the solvents the oil
  9. customwas purified by MPLC (15%ethyl acetate, hexane, silica)

Sources & evidence

ORD record
ord-db4d5df141a742968cfb5435858e3497
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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