m-Chloroperbenzoic acid → HCID 59568673, compound

HRID 1848517Notes

Reaction equation

HRID 1848517 reaction equation
[CH:1]1([C:4]2[C:12]3[CH2:11][O:10][C:9](=[O:13])[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:14]=[CH2:15])[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1>C(Cl)Cl>[CH:1]1([C:4]2[C:12]3[CH2:11][O:10][C:9](=[O:13])[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:14]2[CH2:15][O:24]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 666439474-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one

Product 1

HCID 59568673HCID 59568673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-cyclopropyl-5-vinyl-2-benzofuran-1(3H)-one (440 mg, 2.2 mmol) in 50 mL of DCM was slowly added mCPBA (1.14 g, 6.6 mmol) in 50 mL of DCM at 0° C. After warming to room temperature, the mixture was stirred for 12 hours. The mixture was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers were combined, washed with brine and then concentrated. The residue was purified via prep-TLC to give the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.77 (d, J=8.6 Hz, 1H), 7.39 (d, J=7.8 Hz, 1H), 5.39 (s, 2H), 4.43-4.45 (m, 1H), 3.26-3.28 (m, 1H), 2.68-2.70 (m, 1H), 1.94-2.01 (m, 1H), 1.08-1.12 (m, 2H), 0.65-0.75 (m, 2H).

Workup

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washwashed with brine
  4. concentrationconcentrated
  5. customThe residue was purified via prep-TLC

Sources & evidence

ORD record
ord-ece2c4defe8244edb315be884ebd06a0
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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