1-Methylimidazole → HCID 25197112, compound

HRID 1993467Notes

Reaction equation

HRID 1993467 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[CH:8]=[C:7]3[O:13][C:14]([CH3:18])([CH3:17])[CH:15]=[CH:16][C:6]3=[CH:5][C:4]=2[N:3]=1.CN1C=CN=C1.Cl[O-].[Na+].S([O-])([O-])(=[O:30])=S.[Na+].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[CH:8]=[C:7]3[O:13][C:14]([CH3:18])([CH3:17])[C@H:15]4[O:30][C@H:16]4[C:6]3=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite2×HCID 59134347HCID 59134347, compound

Product 1

HCID 25197112HCID 25197112, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-2,2,9-trimethyl-2H-pyrano[2,3-g]quinoline (200 mg, 0.77 mmol) in ethyl acetate (3.0 mL), N-methyl imidazole (0.012 mL, 0.154 mmol) and ent-Ph,Ph salen manganese complex (8.0 mg, 0.0077 mmol) were added at room temperature and aqueous sodium hypochlorite solution (1.0 g, 1.513 mol/kg, 1.54 mmol) was added dropwise, and the resulting mixture was stirred for 40 minutes. Aqueous sodium hypochlorite solution (1.0 g, 1.513 mol/kg, 1.54 mmol) was added dropwise, and the resulting mixture was further stirred at room temperature for 30 minutes. Upon the completion of the reaction, aqueous sodium thiosulfate solution was added to the reaction solution, the resulting solution was filtered through celite and extracted. The organic phase was washed with aqueous sodium hydrogencarbonate solution and then with aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=10/1) to obtain (3S*,4S*)-7-chloro-3,4-epoxy-2,2,9-trimethyl-3,4-dihydro-2H-pyrano[2,3-g]quinoline (yield: 94%).

Workup

  1. stirringthe resulting mixture was further stirred at room temperature for 30 minutes
  2. additionwas added to the reaction solution
  3. filtrationthe resulting solution was filtered through celite
  4. extractionextracted
  5. washThe organic phase was washed with aqueous sodium hydrogencarbonate solution
  6. dry with materialwith aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was purified by column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-07934d633710491091e849aa9bb23f6f
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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