Hydrogen Peroxide → HCID 11356211, compound

HRID 430759Notes

Reaction equation

HRID 430759 reaction equation
[CH2:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[O:6][CH:5]=1)[CH:2]=[CH2:3].CSC.B.[OH-:19].[Na+].OO.[Cl-].[NH4+]>O1CCCC1.C(O)C>[OH:19][CH2:3][CH2:2][CH2:1][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[O:6][CH:5]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 15307495HCID 15307495, compound

Product 1

HCID 11356211HCID 11356211, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-(2-propenyl)-7-methoxybenzofuran (2.19 g) was dissolved in anhydrous tetrahydrofuran (25 ml) under argon atmosphere and the solution was cooled to 0° C. Borane dimethylsulfide complex (2M solution in THF, 6.1 ml) was added and the solution was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and ethanol (20 ml), 3N aqueous sodium hydroxide solution (1.3 ml) and 30% hydrogen peroxide solution (1.5 ml) were added. After stirring the reaction solution at room temperature for another 15 minutes, the reaction mixture was poured into saturated aqueous ammonium chloride solution, and the resultant was extracted with ethyl acetate. The organic layer was washed with water and with saturated brine, and dried over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: cyclohexane/ethyl acetate=3/1-2/1) to obtain the desired compound (1.42 g, yield: 59%).

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. stirringAfter stirring the reaction solution at room temperature for another 15 minutes
  3. extractionthe resultant was extracted with ethyl acetate
  4. washThe organic layer was washed with water and with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removing the sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (solvent: cyclohexane/ethyl acetate=3/1-2/1)

Sources & evidence

ORD record
ord-94b2f22c205841d69de92a487150eff2
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

Loading…