Sodium Chloride → HCID 18950723, compound

HRID 1492562Notes

Reaction equation

HRID 1492562 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.[CH3:27][O:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34](CBr)=[CH:33][CH:32]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1.CCCCCC>[CH3:27][O:28][CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:20][C:19]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[O:22])=[CH:33][CH:32]=1

Participants

9

Reactant 6

HCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 2724141Tetrabutylammonium FluorideHCID 11469818HCID 11469818, compoundHCID 141181971-(Bromomethyl)-4-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Product 1

HCID 18950723HCID 18950723, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Procedure

In argon atmosphere, 2.02 g of diisopropylamine was dissolved in 50 ml of dry tetrahydrofuran, followed by dropwise addition of the solution of 12.5 ml of 1.55M n-butyl lithium in hexane at -20° C., which was then stirred at the same temperature for five minutes and cooled subsequently. 2-(3-pyridyl)-2-(trimethylsiloxy)acetonitrile (4.13 g) dissolved in 20 ml of dry tetrahydrofuran was added dropwise. After stirring at the same temperature for one hour, the reaction mixture was dissolved in 10 ml of tetrahydrofuran. 4-Bromomethylphenyl methoxymethyl ether (4.48 g) was added dropwise, and the temperature was gradually increased from -78° C. to room temperature, followed by stirring overnight. The 20.0 ml of the solution of 1.0M tetra-n-butylammonium fluoride of tetrahydrofuran 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 in aqueous sodium Chloride, dried over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The obtained residue was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (2:98 v/v) was obtained 2.30 g of 2-(4-methoxymethyloxyphenyl)-1-(3-pyridyl)ethanone.

Workup

  1. temperaturecooled subsequently
  2. additionwas added dropwise
  3. stirringAfter stirring at the same temperature for one hour
  4. temperaturethe temperature was gradually increased from -78° C. to room temperature
  5. stirringby stirring overnight
  6. stirringstirred for 3.5 hours
  7. customthe organic phase was separated which
  8. extractionwas then extracted with ethyl acetate from aqueous phase
  9. washwashed in aqueous sodium Chloride
  10. dry with materialdried over magnesium sulfate
  11. distillationThen, the solvent was distilled off under reduced pressure
  12. washfrom a fraction eluted with methanol-methylene chloride (2:98 v/v)

Sources & evidence

ORD record
ord-b066a500292c47c5b12108aec652fa61
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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