Iodobenzene → 2-Phenyl-2,3-dihydrofuran

HRID 368912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 368912
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]=1

Komponenten

9

Edukt 4

HCID 11575IodobenzeneHCID 11776TriphenylphosphineHCID 709342,3-DihydrofuranHCID 517044Potassium Acetate

Produkt 1

HCID 108880522-Phenyl-2,3-dihydrofuranAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customThe contents of the flask were irradiated for 6.00 min with an effect of 60 W
  2. temperatureAfter cooling
  3. extractionwas extracted three times with 25 ml DCM
  4. washThe combined extracts were washed with 25 ml water
  5. concentrationconcentrated to an oil
  6. customThe crude product was purified by column chromatography on silica gel using pentaneldiethyl ether (19/1) as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-ecee3b0fcc474c9593d591808a029019
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06136157

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