Iodobenzene → 2-Phenyl-2,3-dihydrofuran

HRID 368912노트

반응식

HRID 368912 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ecee3b0fcc474c9593d591808a029019
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136157

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