Sodium Chloride → HCID 54503053, compound

HRID 1492522Notes

Reaction equation

HRID 1492522 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([O:22][Si](C)(C)C)[C:20]#N)[CH:14]=1.BrC[C:29]1[CH:41]=[CH:40][C:32]([CH:33]=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][CH:30]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1.CCCCCC>[O:22]=[C:19]([C:15]1[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=1)[CH2:20][C:29]1[CH:41]=[CH:40][C:32]([CH:33]=[CH:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:31][CH:30]=1

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 2724141Tetrabutylammonium FluorideHCID 11469818HCID 11469818, compoundHCID 248203732-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 54503053HCID 54503053, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

In argon atmosphere, 4.88 g of diisopropylamine was dissolved in 100 ml of dry tetrahydrofuran, followed by dropwise addition of 1.55M n-butyl lithium in 31.1 ml of hexane in solution at -20° C. After stirring at the same temperature for 10 minutes and then cooling down to -78° C., 9.96 g of 2-(3-pyridyl)-2-(trimethylsiloxy)acetonitrile dissolved in 100 ml of dry tetrahydrofuran was added dropwise. After stirring at the same temperature for one hour, 12.99 g of ethyl 4-bromomethylcinnamate dissolved in 100 ml of dry tetrahydrofuran was added, followed by gradual temperature rise from -78° C. to room temperature and stirring overnight. 1.0M Tetra-n-butylammonium fluoride in 48.3 ml of tetrahydrofuran in solution was added and stirred for 3.5 hours. To the reaction mixture was added saturated aqueous sodium chloride solution, and the organic phase was separated, which was then extracted with ethyl acetate from aqueous phase. The organic phases were combined and washed with saturated aqueous sodium chloride solution, followed by drying over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, and 6.21 g of ethyl 4-[2-oxo-2-(3-pyridyl)ethyl]cinnamate was obtained from a fraction eluted with methanol-methylene chloride (2:98 v/v) .

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at the same temperature for one hour
  3. additionwas added
  4. customfollowed by gradual temperature rise from -78° C. to room temperature
  5. stirringstirring overnight
  6. stirringstirred for 3.5 hours
  7. customthe organic phase was separated
  8. extractionwhich was then extracted with ethyl acetate from aqueous phase
  9. washwashed with saturated aqueous sodium chloride solution
  10. dry with materialby drying over magnesium sulfate
  11. distillationThen, the solvent was distilled off under reduced pressure
  12. customThe residue obtained

Sources & evidence

ORD record
ord-c8fef0155afc42e5a678b1116dab6002
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…