m-Chloroperbenzoic acid → 6-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one

HRID 1466095Notes

Reaction equation

HRID 1466095 reaction equation
[CH:1]([C:3]1[C:12]([CH3:13])=[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:22])C=1>C(Cl)Cl>[CH3:13][C:12]1[C:3]([CH:1]2[CH2:2][O:22]2)=[CH:4][C:5]2[CH2:9][O:8][C:7](=[O:10])[C:6]=2[CH:11]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666438115-ethenyl-6-methyl-2-benzofuran-1(3H)-one

Product 1

HCID 595686626-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-ethenyl-6-methyl-2-benzofuran-1(3H)-one (1.00 g, 5.75 mmol) in 50 mL of DCM was slowly added m-CPBA (3.50 g, 17.4 mmol) in 50 mL of DCM at 0° C. The mixture was warmed to room temperature, and stirred for 2 days. The mixture was washed with aqueous Na2SO3 until KI indicator paper didn't change color. The organic layer was washed with brine and then concentrated. The residue was purified via silica column to give product 6-methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one. LC/MS (IE, m/z): [M+1]+=191.

Workup

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI indicator paper didn't change color
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified via silica column

Sources & evidence

ORD record
ord-552f1ab466884a68a2b1416b2b3c1b10
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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