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

HRID 1901121ノート

反応式

HRID 1901121 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.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

参加物

9

反応物 4

HCID 8028TetrahydrofuranHCID 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 4

HCID 24385Nickel Dichloride触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7370116fc9a84715ad717391f22689a5
出典データセット
uspto-grants-1996_11
特許番号
US05576338

反応ノート

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