m-Chloroperbenzoic acid → 4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

HRID 515106Notes

Reaction equation

HRID 515106 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[O:8][CH2:9][C:5]=2[C:4]=1[CH3:13])=[CH2:2].ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:13][C:4]1[C:5]2[CH2:9][O:8][C:7](=[O:10])[C:6]=2[CH:11]=[CH:12][C:3]=1[CH:1]1[CH2:2][O:22]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666439224-methyl-5-vinylisobenzofuran-1(3H)-one

Product 1

HCID 552705554-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-ethenyl-4-methyl-2-benzofuran-1(3H)-one (1.5 g, 8.4 mmol) was added to DCM (25 mL) at 0° C. then meta-chloroperbenzoic acid (2.9 g, 17 mmol) was added and the mixture was stirred at room temperature overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, saturated sodium bicarbonate, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system) to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one.

Workup

  1. washThe reaction mixture was washed once each with saturated aqueous Na2S2O3, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude material was purified by MPLC chromatography (eluting with 0-80% EtOAc/hexane solvent system)

Sources & evidence

ORD record
ord-6d2fc5545159459da5eddd34c1e521c4
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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