Sodium Chloride → HCID 18950671, compound

HRID 1492518Notes

Reaction equation

HRID 1492518 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]([O:33][CH2:34][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]([O:33][CH2:34][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 12870369Ethyl 2-[4-(bromomethyl)phenoxy]acetateHCID 178418339Butyllithium

Product 1

HCID 18950671HCID 18950671, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Procedure

In argon atmosphere, 7.60 g of diisopropylamine was dissolved in 100 ml of dry tetrahydrofuran, followed by dropwise addition of 1.55M n-butyl lithium in 48.4 ml of hexane in solution at -20° C., which was then agitated at the same temperature for 15 minutes, subsequently followed by cooling to -78° C. and by subsequent dropwise addition of 15.48 g of 2-(3-pyridyl)-2-(trimethylsiloxy)acetonitrile dissolved in 150 ml of dry tetrahydrofuran over 10 minutes. After agitation at the same temperature for 30 minutes, the addition of 20.50 g of ethyl 4-(bromomethyl)phenoxyacetate dissolved in 30 ml of tetrahydrofuran over 10 minutes, the temperature was gradually raised from -78° C. to room temperature, followed by stirring overnight. Then, 1.0M tetra-n-butylammonium fluoride in 75.1 ml of tetrahydrofuran in solution was added, followed by agitation for five hours. To the resulting reaction mixture was added aqueous saturated solution of sodium chloride, followed by separation of the organic phase, which was then extracted with ethyl acetate from aqueous phase. The organic phases were combined, then washed in aqueous saturated solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column, to yield 13.20 g of ethyl 4-[2-oxo-2-(3-pyridyl)ethyl]phenoxyacetate from a fraction eluted with methanol-chloroform (2:98 v/v).

Workup

  1. waitAfter agitation at the same temperature for 30 minutes
  2. temperaturethe temperature was gradually raised from -78° C. to room temperature
  3. stirringby stirring overnight
  4. waitfollowed by agitation for five hours
  5. customTo the resulting reaction mixture
  6. customfollowed by separation of the organic phase, which
  7. extractionwas then extracted with ethyl acetate from aqueous phase
  8. washwashed in aqueous saturated solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue obtained

Sources & evidence

ORD record
ord-b19caf61102c48f5a823a817eeee5345
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…