Oxygen → 6,7-Dichloro-2,3-dimethoxy-5-formylquinoxaline

HRID 1957123Notes

Reaction equation

HRID 1957123 reaction equation
O=[O+][O-].[O:4]=O.[Cl:6][C:7]1[C:8]([CH:22]=C)=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:17])[N:13]=[C:12]([O:18][CH3:19])[C:11]([O:20][CH3:21])=[N:10]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:6][C:7]1[C:8]([CH:22]=[O:4])=[C:9]2[C:14](=[CH:15][C:16]=1[Cl:17])[N:13]=[C:12]([O:18][CH3:19])[C:11]([O:20][CH3:21])=[N:10]2

Participants

6

Reactant 4

HCID 977OxygenHCID 11776TriphenylphosphineHCID 24823OzoneHCID 10636850HCID 10636850, compound

Product 1

HCID 104934926,7-Dichloro-2,3-dimethoxy-5-formylquinoxalineYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ozone and oxygen was bubbled gently through a stirred solution of 6,7-dichloro-2,3-dimethoxy-5-ethenylquinoxaline (1.76 g, 6.2 mmol) in chloroform (200 mL) at -60° C. until a blue colour persisted. The solution was purged with nitrogen, and then triphenylphosphine (3.23 g, 12.3 mmol) was added. The mixture was allowed to warm to room temperature and stirred for a further 16 hours. The chloroform was removed under reduced pressure and the residue purified by flash chromatography (eluting with toluene) to give 6,7-dichloro-2,3-dimethoxy-5-formylquinoxaline (1.60 g, 90%) as a fluffy white solid.

Workup

  1. customThe solution was purged with nitrogen
  2. customThe chloroform was removed under reduced pressure
  3. customthe residue purified by flash chromatography (eluting with toluene)

Sources & evidence

ORD record
ord-7969d5bcd2194c96a6deb3c6606ab96d
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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