Hydrogen Peroxide → HCID 18519066, compound

HRID 1369284Notes

Reaction equation

HRID 1369284 reaction equation
[C:1]([O:4][CH:5]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[C:12]3[C:17](=[CH:18][C:6]1=2)[C:16]([CH:19]=[O:20])=[CH:15][CH:14]=[CH:13]3)(=[O:3])[CH3:2].OO.[O-:23]Cl=O.[Na+]>CC#N.O.[NH4+].[Cl-]>[C:1]([O:4][CH:5]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[C:12]3[C:17](=[CH:18][C:6]1=2)[C:16]([C:19]([OH:23])=[O:20])=[CH:15][CH:14]=[CH:13]3)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 18519037HCID 18519037, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 18519066HCID 18519066, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3-acetoxy-5-formylnaphtho[2,3-c]furan-1(3H)-one (100 mg, 0.377 mmol) in MeCN (0.373 mL) and H2O (0.150 mL) at rt was added NaH2PO4 (15.3 mg, 0.097 mmol) followed by 50% H2O2 (0.026 mL). NaClO2 (1.0 M in H2O, 0.518 mL) was added over the course of 2 h via syringe pump. The reaction mixture was then diluted with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to give the title compound (87 mg, 80%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c4d43dd68eef460dbed990f5277e380e
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

Loading…