m-Chloroperbenzoic acid → HCID 59568700, compound

HRID 1474325Notes

Reaction equation

HRID 1474325 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[C:5]([CH3:12])=[CH:4][C:3]=1[CH:13]=[CH2:14].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[C:5]([CH3:12])=[CH:4][C:3]=1[CH:13]1[CH2:14][O:23]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643943HCID 66643943, compound

Product 1

HCID 59568700HCID 59568700, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,7-dimethyl-5-vinyl-2-benzofuran-1(3H)-one (0.4 g, 2.1 mmol) in 60 mL of DCM was slowly added mCPBA (85%, 0.7 g, 4.2 mmol) at 0° C. After warming to room temperature, the mixture was stirred for 48 hours. The mixture was washed subsequently with saturated NaHCO3, aqueous Na2SO3, 5% NaOH and brine. The mixture was concentrated and the residue was purified by column chromatography to afford 4,7-dimethyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one as white solid.

Workup

  1. customat 0° C
  2. washThe mixture was washed subsequently with saturated NaHCO3, aqueous Na2SO3, 5% NaOH and brine
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cabc3f406ccd449bace63aee4fedeb89
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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