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

HRID 1901121Notes

Reaction equation

HRID 1901121 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7370116fc9a84715ad717391f22689a5
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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