Tetrahydrofuran → 4-(Furan-3-yl)-7-methylquinoline

HRID 1901121노트

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HRID 1901121 반응식
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:16]=[CH:15][O:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C[Mg+].[Br-].[CH2:20]1COCC1.[NH4+].[Cl-]>CCOCC.Cl[Ni]Cl.O.C1(C)C=CC=CC=1>[O:14]1[CH:15]=[CH:16][C:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:20])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:13]1

참가 물질

9

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 233701774-(Furan-3-yl)-7-methylquinoline

시약·촉매·용매 4

HCID 24385Nickel Dichloride촉매HCID 962Water용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

To a mixture of 7-chloro-4-(3-furyl)quinoline (30.2 g) and NiCl2 (dppp) (7.1 g) in Et2O (950 mL) was added MeMgBr (141 mL of a 1.4M solution in 3:1 THF:toluene) at such a rate to maintain a temperature of 30° C. The mixture was refluxed for 30 min., cooled to 0° C. and saturated NH4Cl (200 mL) was added followed by H2O (100 mL). The layers were separated and the aqueous phase was extracted with EtOAc. The combined organics were washed with NH4OAc buffer, brine, dried (MgSO4) and concentrated. Chromatography (silica gel; EtOAc/hexane (3:7)) provided the title compound as a beige oil.

후처리

  1. temperatureThe mixture was refluxed for 30 min.
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organics were washed with NH4OAc buffer, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7370116fc9a84715ad717391f22689a5
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576338

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