1-Methylimidazole → HCID 25197112, compound

HRID 2425348Notes

Reaction equation

HRID 2425348 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.O>[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

7

Reactant 4

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

Product 1

HCID 25197112HCID 25197112, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×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 sodium hypochlorite aqueous solution (1.0 g, 1.513 mol/kg, 1.54 mmol) was added dropwise in water bath, and the resulting mixture was stirred in water bath for 40 minutes. In water bath, sodium hypochlorite aqueous solution (1.0 g, 1.513 mol/kg, 1.54 mmol) was added dropwise, and the resulting mixture was further stirred in water bath for 30 minutes. Upon the completion of the reaction, sodium thiosulfate aqueous solution was added to the reaction solution, the resulting solution was filtered through celite and extracted. The organic phase was washed with sodium hydrogencarbonate aqueous solution and then with sodium chloride aqueous 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. additionwas added to the reaction solution
  2. filtrationthe resulting solution was filtered through celite
  3. extractionextracted
  4. washThe organic phase was washed with sodium hydrogencarbonate aqueous solution
  5. dry with materialwith sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent
  7. customthe residue was purified by column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-42fc5b5b96cb4556852e4c2a1db51829
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

Loading…