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

HRID 741838노트

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HRID 741838 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.[CH3:17][Mg+].[Br-].[NH4+].[Cl-].O>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[O:14]1[CH:15]=[CH:16][C:12]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:17])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:13]1

참가 물질

7

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 178418745HCID 178418745, 화합물촉매HCID 3283Diethyl Ether용매

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온도
30 °C

실험 절차

To a mixture of 7-chloro-4-(furan-3-yl)quinoline (30.2 g) and [1,3-bis(diphenylphosphino)propane]nickel (II) chloride (7.1 g) in Et2O (950 mL) was added MeMgBr (141 mL, 1.4M 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. temperaturecooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organics were washed with NH4OAc buffer, brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-07cefc43d8834002ad853d126d18dce2
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552437

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