m-Chloroperbenzoic acid → HCID 77231249, compound

HRID 1501744Notes

Reaction equation

HRID 1501744 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-f123fc442caf45b18ee6d8b54639eecf
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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