Tetrahydrofuran → HCID 14823235, compound

HRID 1031501Notes

Reaction equation

HRID 1031501 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.CCCCCC.C([Li])CCC.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#N)=[CH:32][N:31]=2)=[CH:26][CH:25]=1.[O:38]1CCCC1>CO>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:38])[C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=3)=[CH:32][N:31]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8058HexaneHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 148232346-(4-Chlorophenyl)pyridine-3-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 14823235HCID 14823235, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In dry tetrahydrofuran (10 ml) was dissolved 4-bromoveratrol (1.2 g). To the solution was added dropwise slowly an n-hexane solution (3.7 ml) of 15% n-butyllithium, while stirring under cooling at -68° C. to -70° C. under an atmosphere of nitrogen gas. The mixture was stirred for 20 minutes at the same temperature range for 20 minutes. Then there was added dropwise in the course of 30 minutes a solution of 2-(4-chlorophenyl)-5-cyanopyridine (0.8 g) in dry tetrahydrofuran (8 ml). The mixture was stirred at the same temperature range for 30 minutes, followed by addition of methanol (6 ml), and warming to the room temperature, slowly. The reaction mixture was concentrated, and there was added ethyl acetate (100 ml), and the solution was washed with ice-water (30 ml) once, to which was added silica gel (60 g), followed by stirring at room temperatures for 2 hours. The reaction mixture was then left standing overnight, and the silica gel was filtered off. To the filtrate was added anhydrous magnesium sulfate for drying, and the filtrate was subjected to filtration. The filtrate was concentrated, and the concentrate was purified by means of a silica gel chromatography (eluted with chloroform), followed by recrystallization from acetonitrile to obtain 2-(4-chlorophenyl)-5-(3,4-dimethoxybenzoyl)pridine (700 mg) as pale yellow granular crystals, m.p. 168° to 170° C.

Workup

  1. temperatureunder cooling at -68° C. to -70° C. under an atmosphere of nitrogen gas
  2. stirringThe mixture was stirred for 20 minutes at the same temperature range for 20 minutes
  3. stirringThe mixture was stirred at the same temperature range for 30 minutes
  4. concentrationThe reaction mixture was concentrated
  5. additionthere was added ethyl acetate (100 ml)
  6. washthe solution was washed with ice-water (30 ml) once
  7. additionto which was added silica gel (60 g)
  8. stirringby stirring at room temperatures for 2 hours
  9. waitThe reaction mixture was then left
  10. filtrationthe silica gel was filtered off
  11. additionTo the filtrate was added anhydrous magnesium sulfate
  12. customfor drying
  13. filtrationthe filtrate was subjected to filtration
  14. concentrationThe filtrate was concentrated
  15. customthe concentrate was purified by means of a silica gel chromatography (eluted with chloroform)
  16. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-4c801929001c4559b64f4560fce9c141
Source dataset
uspto-grants-1990_09
Patent number
US04954497

Reaction notes

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