Iodobenzene → 2-Phenyl-2,3-dihydrofuran

HRID 368912ノート

反応式

HRID 368912 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 108880522-Phenyl-2,3-dihydrofuran収率 58%

試薬・触媒・溶媒 4

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ecee3b0fcc474c9593d591808a029019
出典データセット
uspto-grants-2000_10
特許番号
US06136157

反応ノート

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