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

HRID 741838ノート

反応式

HRID 741838 の反応式
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

参加物

7

反応物 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 233701707-Chloro-4-(furan-3-yl)quinolineHCID 178418689HCID 178418689、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418745HCID 178418745、化合物触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
30 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07cefc43d8834002ad853d126d18dce2
出典データセット
uspto-grants-1996_09
特許番号
US05552437

反応ノート

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