Iodobenzene → 2-phenyl-2,3-dihydrofuran
Reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[CH:12]=[CH:11][CH2:10][CH2:9]1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[C:2]1([CH:12]2[CH2:11][CH:10]=[CH:9][O:8]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
Table 1, Entry 5. In the reaction tube were mixed iodobenzene (0.102 g, 0.5 mmol), dihydrofuran (0.350 g, 5.0 mmol), palladium acetate (0.00281 g, 0.0125 mmol), potassium acetate (0.147 g,1.5 mmol), n-Bu4NCl (0.139 g, 0.5 mmol), triphenylphosphine (0.00328 g, 0.0125 mmol) and 1.0 ml DMF.under nitrogen. The contents of the flask were irradiated for 6.00 min with an effect of 60 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml DCM. The combined extracts were washed with 25 ml water and concentrated to an oil. The crude product was purified by column chromatography on silica gel using pentaneldiethyl ether (19/1) as the eluent. The yield was 58% (yellow oil).
Workup
- customThe contents of the flask were irradiated for 6.00 min with an effect of 60 W
- temperatureAfter cooling
- extractionwas extracted three times with 25 ml DCM
- washThe combined extracts were washed with 25 ml water
- concentrationconcentrated to an oil
- customThe crude product was purified by column chromatography on silica gel using pentaneldiethyl ether (19/1) as the eluent
Sources & evidence
- ORD record
- ord-ecee3b0fcc474c9593d591808a029019
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06136157
Reaction notes
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