Hydrogen Peroxide → HCID 22618299, compound

HRID 842115Notes

Reaction equation

HRID 842115 reaction equation
[CH2:1]([C:8]1[O:9][C:10]2[C:16]([CH2:17][CH:18]=[CH2:19])=[CH:15][C:14]([Cl:20])=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(BCCC(C)C)CC(C)C.[OH-:32].[Na+].OO>C1COCC1>[CH2:1]([C:8]1[O:9][C:10]2[C:16]([CH2:17][CH2:18][CH2:19][OH:32])=[CH:15][C:14]([Cl:20])=[CH:13][C:11]=2[N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22618304HCID 22618304, compoundHCID 178442031HCID 178442031, compound

Product 1

HCID 22618299HCID 22618299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-benzyl-5-chloro-7-allylbenzoxazole (2.2 g, 8 mmol) in THF (12 ml) was added to a solution of di-iso-amylborane (1.13 g, 8 mmol) in THF. The reaction was allowed to stir at room temperature for 21 hours and then 3 N sodium hydroxide solution (4 ml) was added followed by 30% hydrogen peroxide (4 ml). After 3 hours, the reaction mixture was partitioned between dichloromethane and water. The dichloromethane solution was washed with water (3×100 ml) and the solvent was evaporated under reduced pressure. The residue was purified over flash chromatographic silica gel to give the title compound (600 mg) eluted with 1:1 dichloromethane/hexane. The material was recrystallized three times from toluene to give the title compound (200 mg), trip 78-80° C.

Workup

  1. waitAfter 3 hours
  2. customthe reaction mixture was partitioned between dichloromethane and water
  3. washThe dichloromethane solution was washed with water (3×100 ml)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified over flash chromatographic silica gel

Sources & evidence

ORD record
ord-2c46cc94c1e5447399c4b928064b6c4c
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

Loading…