Sodium Chloride → HCID 18950665, compound

HRID 1492527Notes

Reaction equation

HRID 1492527 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([O:10][Si](C)(C)C)[C:8]#N)[CH:2]=1.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22](CBr)=[CH:21][CH:20]=1)=[O:18].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1>[O:10]=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:8][C:22]1[CH:23]=[CH:24][C:19]([C:17]([O:16][CH3:15])=[O:18])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 2724141Tetrabutylammonium FluorideHCID 11469818HCID 11469818, compound

Product 1

HCID 18950665HCID 18950665, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of diisopropylamine (4.5 g) in dry tetrahydrofuran (60 ml) was cooled to -35 to 31 40 ° C., followed by addition of 1.5M n-butyl lithium in 30 ml of hexane in solution, and stirred for 30 minutes, to produce lithium diisopropylamide. To the solution was added a solution of 2-(3-pyridyl)-2-(trimethylsiloxy)acetonitrile in dry tetrahydrofuran at -78 ° C., and stirred at the same temperature for 30 minutes. After the addition of a solution of methyl 4-bromomethyl benzoate in dry tetrahydrofuran at - 78 ° C., stirring was effected overnight at -78 ° C. to room temperature. To the reaction mixture obtained was added 1.0 M tetra-n-butylammonium fluoride in 40 ml of dry tetrahydrofuran in solution and stirred at room temperature for 3.5 hours. The reaction solution was poured into saturated aqueous sodium chloride solution, and after separation of the organic phase, the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed in saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate and distillation of the solvent. The residue was subjected to chromatography on a silica gel column. A fraction eluted with chloroform-methanol (50:1 v/v) was recrystallized in n-hexane chloroform to produce 3.0 g of methyl 4-[2-oxo-2-(3-pyridyl)ethyl]benzoate.

Workup

  1. stirringstirring
  2. waitwas effected overnight at -78 ° C. to room temperature
  3. customTo the reaction mixture obtained
  4. stirringstirred at room temperature for 3.5 hours
  5. customafter separation of the organic phase
  6. extractionthe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic phases were washed in saturated aqueous sodium chloride solution
  8. dry with materialby drying over magnesium sulfate and distillation of the solvent
  9. washA fraction eluted with chloroform-methanol (50:1 v/v)
  10. customwas recrystallized in n-hexane chloroform

Sources & evidence

ORD record
ord-bb7b34cd9f404538843a8bed6d8954ee
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…