Sodium hydride → HCID 15381168, compound

HRID 849322Notes

Reaction equation

HRID 849322 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].Br[CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.[Cl-].[NH4+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Product 1

HCID 15381168HCID 15381168, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 50.8 g of 3,4-dichlorophenylacetonitrile in 250 ml of THF is added dropwise at a temperature below 20° C. to a suspension of 12 g of sodium hydride (55% dispersion in oil) in 175 ml of THF and the reaction mixture is stirred for 2 hours at RT. It is cooled to -20° C., a solution of 62.5 g of 1-bromo-3-(tetrahydropyran-2-yloxy)propane in 60 ml of THF is added dropwise and the reaction mixture is stirred while the temperature is allowed to rise to RT. It is poured into a solution of 31 g of ammonium chloride in 1.4 liters of water and extracted with ether, the combined organic phases are washed with saturated NaCl solution and dried over MgSO4 and the solvents are evaporated off under vacuum. The residue is chromatographed on silica using toluene and then a toluene/AcOEt mixture (95/5; v/v) as the eluent to give 64 g of the expected product, which is used as such.

Workup

  1. temperatureIt is cooled to -20° C.
  2. stirringthe reaction mixture is stirred while the temperature
  3. customto rise to RT
  4. extractionextracted with ether
  5. washthe combined organic phases are washed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customthe solvents are evaporated off under vacuum
  8. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-16c4e25fc98342c29eee0ebd445490b8
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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