m-Chloroperbenzoic acid → HCID 77231249, compound

HRID 1848426Notes

Reaction equation

HRID 1848426 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[C:4]=1[CH2:13][CH2:14][OH:15])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:24])C=1>ClCCl>[OH:15][CH2:14][CH2:13][C:4]1[C:5]2[CH2:9][O:8][C:7](=[O:10])[C:6]=2[CH:11]=[CH:12][C:3]=1[CH:1]1[CH2:2][O:24]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66646404HCID 66646404, compound

Product 1

HCID 77231249HCID 77231249, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Ethenyl-4-(2-hydroxyethyl)-2-benzofuran-1(3H)-one (1.2 g, 5.9 mmol) was added to a flask containing a stir bar. To the flask was then added dichloromethane (20 mL). The flask was placed in a cool bath of 0° C.; to the flask was poured mCPBA (1.5 g, 8.8 mmol) and the resulting mixture was stirred at room temperature for overnight; LC as well as TLC (hexanes/EtOAc=1/1) indicated that reaction had gone to completion. The solution was treated with dichloromethane and washed with NaHCO3, Na2S2O3, and water, the organic layer was then dried over Na2SO4, filtered and concentrated to dryness, it was then treated with AcOH (20 mL) and stirred overnight; LC indicated formation of cyclized product. The solvent was removed and the resulting residue was absorbed onto silica gel and the title compound was isolated with the solvent system of hexanes/EtOAc (1/1).

Workup

  1. additioncontaining a stir bar
  2. customThe flask was placed in a cool bath of 0° C.
  3. washwashed with NaHCO3, Na2S2O3, and water
  4. dry with materialthe organic layer was then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness, it
  7. additionwas then treated with AcOH (20 mL)
  8. stirringstirred overnight
  9. customThe solvent was removed
  10. customthe resulting residue was absorbed onto silica gel

Sources & evidence

ORD record
ord-85902392cce74aef81a618579c5ec7c3
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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