m-Chloroperbenzoic acid → 5-(oxiran-2-yl)-2-benzofuran-1(3H)-one

HRID 1501925Notes

Reaction equation

HRID 1501925 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[CH:4]=1)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[O:21]1[CH2:2][CH:1]1[C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[O:8][CH2:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 211063135-ethenyl-2-benzofuran-1(3H)-one

Product 1

HCID 595687155-(oxiran-2-yl)-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Ethenyl-2-benzofuran-1(3H)-one (28.4 g, 177 mmol) was dissolved in DCM (400 mL) then mCPBA (47.7 g, 213 mmol) was added. The mixture was stirred at room temperature overnight. Some starting olefin remained. Another 25 g of mCPBA was added and the mixture was stirred overnight. The mixture was poured into ice cold Na2SO3 solution (saturated). The layers were separated and the organic layer was washed with 5% NaOH solution, brine, then was dried (MgSO4). The crude product was purified by MPLC (330 g column, eluting with 40% EtOAc/hexane, 2 L, then with 45% EtOAc/hexane, 2 L, to afford 5-(oxiran-2-yl)-2-benzofuran-1(3H)-one. LC-MS: M+1=177.

Workup

  1. stirringthe mixture was stirred overnight
  2. additionThe mixture was poured into ice cold Na2SO3 solution (saturated)
  3. customThe layers were separated
  4. washthe organic layer was washed with 5% NaOH solution, brine
  5. dry with materialwas dried (MgSO4)
  6. customThe crude product was purified by MPLC (330 g column
  7. washeluting with 40% EtOAc/hexane, 2 L

Sources & evidence

ORD record
ord-d98f978d96574fac8ca5ed36e1696cfa
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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