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

HRID 1466087Notes

Reaction equation

HRID 1466087 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].C1C=C(Cl)C=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 (1.46 g, 8.38 mmol) was added to DCM (25 mL) at 0° C. then m-CPBA (2.89 g, 16.8 mmol) was added and the mixture was stirred at RT overnight. The reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and evaporated to dryness. The crude material was purified by MPLC chromatography through 120 g Redi-sep column eluting with 0-80% EtOAc/hexane solvent system to yield 4-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. 1H-NMR (500 MHz, CDCl3): δ ppm 7.77 (d, J=8 Hz, 1H), 7.43 (d, J=8 Hz, 1H), 5.30 (s, 2H), 4.12 (s, 1H), 3.27 (t, J=4 Hz, 1H), 2.735 (dd, J=2.2, 5.5 Hz, 1H), 2.43 (s, 3H).

Workup

  1. washThe reaction mixture was washed once each with saturated aqueous Na2S2O3, NaHCO3, 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 through 120 g Redi-sep column
  6. washeluting with 0-80% EtOAc/hexane solvent system

Sources & evidence

ORD record
ord-14eee4b76b4b495081f953154f83b596
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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