m-Chloroperbenzoic acid → HCID 68432696, compound

HRID 1474355Notes

Reaction equation

HRID 1474355 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:24][CH2:2][CH:1]1[C:3]2[C:4](=[C:5]3[CH2:9][O:8][C:7](=[O:10])[C:6]3=[CH:11][CH:12]=2)[CH2:13][CH2:14][O:15]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66646404HCID 66646404, compound

Product 1

HCID 68432696HCID 68432696, 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 into silica gel and 6-(hydroxymethyl)-8,9-dihydro-1H-furo[3,4-f]isochromen-3(6H)-one was isolated with the solvent systems of hexanes/EtOAc (1/1). 1H-NMR (400 MHz, CDCl3) δ ppm 7.807 (d, J=8 Hz, 1H), 7.337 (d, J=8 Hz, 1H), 5.279 (s, 2H), 4.985 (s, 1H), 4.302-4.302 (m, 1H), 4.183-4.084 (m, 2H), 3.954-3.912 (m, 2H), 3.006-2.944 (m, 1H), 2.717-2.686 (m, 1H), 2.179-2.172 (m, 2H)

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 into silica gel

Sources & evidence

ORD record
ord-8a52ab20146243cb89cd2a08c25e6259
Source dataset
uspto-grants-2015_04
Patent number
US09018211B2

Reaction notes

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