Azobisisobutyronitrile → HCID 2784694, compound
Reaction equation
[C:1]1(/[CH:7]=[C:8]2/[C:9](=[O:13])[O:10][CH2:11][CH2:12]/2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].CC(N=NC(C#N)(C)C)(C#N)C>>[C:1]1([CH:7]2[C:8]3([CH2:12][CH2:11][O:10][C:9]3=[O:13])[O:19]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Procedure
To a solution of 3-[1-phenyl-meth-(E)-ylidene]-dihydro-furan-2-one (21a) (4.0 g, 22.9 mmol) and 3-chloroperoxybenzoic acid (6.18 g, 27.6 mmol) in 1,2-dichloroetheane (70 mL) was added catalytic amount of AIBN (50 mg) at 80° C. and refluxed in the dark for 6 h. The resulting solution was cooled and filtered, the solvent was removed under reduced pressure, and the residue dissolved in dichloromethane. The organic phase was washed consecutively with saturated aqueous solutions of NaHCO3 (20 mL), KI (20 mL), Na2S2O3 (20 mL), and NaHCO3 (20 mL) then dried over anhydrous MgSO4 and evaporated under reduced pressure. Product was purified by silica gel flash chromatography using ethyl acetate:petroleum ether (1:4) gave 2.62 g in 60% yield of the title compound.
Workup
- temperaturerefluxed in the dark for 6 h
- temperatureThe resulting solution was cooled
- filtrationfiltered
- customthe solvent was removed under reduced pressure
- dissolutionthe residue dissolved in dichloromethane
- washThe organic phase was washed consecutively with saturated aqueous solutions of NaHCO3 (20 mL), KI (20 mL), Na2S2O3 (20 mL), and NaHCO3 (20 mL)
- dry with materialthen dried over anhydrous MgSO4
- customevaporated under reduced pressure
- customProduct was purified by silica gel flash chromatography
Sources & evidence
- ORD record
- ord-e3eb1c1e8ed7429b86866d1ad2ea9a71
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807677B2
Reaction notes
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