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

HRID 1848421Notes

Reaction equation

HRID 1848421 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 mCPBA (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 the title compound. LC-MS M+1 (calc. 191. found 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-e49d49d6c60941a28bd1113067176fdd
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

Loading…