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

HRID 1502040Notes

Reaction equation

HRID 1502040 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

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 mCPBA (3.50 g, 17.4 mmol) in 50 mL of DCM at 0° C. Warmed to room temperature, the mixture was stirred for 2 days. The mixture was washed with aqueous Na2SO3 until the KI paper didn't change color. The organic layers was washed with brine and then concentrated. The residue was purified via column chromatography to give the product 6-methyl-5-(oxiran-2-yl)-2-benzofuran-1(3H)-one.

Workup

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

Sources & evidence

ORD record
ord-e54279930050494483a61bb50e32faca
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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