m-Chloroperbenzoic acid → HCID 59568684, compound

HRID 1186957Notes

Reaction equation

HRID 1186957 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH2:10][O:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:13]=[CH2:14].ClC1C=C(C=CC=1)C(OO)=[O:20]>ClCCl>[CH3:1][O:2][C:3]1[C:11]2[CH2:10][O:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:13]1[CH2:14][O:20]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66643872HCID 66643872, compound

Product 1

HCID 59568684HCID 59568684, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Methoxy-5-vinyl-2-benzofuran-1(3H)-one (120 mg, 0.63 mmol, 1.0 eq) was added into a 100 mL round bottom flask and dissolved in dichloromethane (5 mL). The solution was cooled to 0° C., and 3-chloroperoxybenzoic acid (327 mg, 1.89 mmol, 2.0 eq) was added portion wise. The mixture was then purged with N2 and stirred at r.t. for 18 hr. To above solution was added water (5 mL). The crude product was extracted with dichloromethane. The organic phase was washed with brine (5 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (hexane/EtOAc 0-50%). The desired product was obtained. 1H NMR (500 MHz, CDCl3, δ in ppm): 7.56 (1H, aromatic, d, J=7.6 Hz), 7.31 (1H, aromatic, d, J=7.6 Hz), 5.50 (2H, m, CH2 lactone), 4.23 (1H, m), 4.02 (3H, s, Me), 3.22 (1H, m), 2.72 (1H, m).

Workup

  1. customThe mixture was then purged with N2
  2. additionTo above solution was added water (5 mL)
  3. extractionThe crude product was extracted with dichloromethane
  4. washThe organic phase was washed with brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (hexane/EtOAc 0-50%)

Sources & evidence

ORD record
ord-3e0c348f76a145ecb2f02a22c120b33e
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

Loading…