Sodium hydride → 2-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran

HRID 342677

Reaction equation

HRID 342677 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Br[CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.[Cl-].[NH4+]>O1CCCC1.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 156708072-(3-Cyano-3-(3,4-dichlorophenyl)propyl)oxytetrahydropyran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

20 g of sodium hydride as a 55-60% dispersion in oil are suspended in 200 ml of dry tetrahydrofuran. A solution of 85 g of 3,4-dichlorophenylacetonitrile in 500 ml of THF is added dropwise at 20° C. in 30 minutes and the reaction mixture is then stirred at RT for 2 hours. It is cooled to -20° C., a solution of 98 g of 2-(2-bromoethoxy)tetrahydropyran in 100 ml of THF is added, the mixture is allowed to return to RT and, after 2 hours, a solution of 50 g of ammonium chloride in 3 liters of water is added. Extraction is carried out with 1.5 liters of ether and the extract is washed with saturated sodium chloride solution, decanted, dried over MgSO4 and concentrated under vacuum.

Workup

  1. temperatureIt is cooled to -20° C.
  2. waitto return to RT and, after 2 hours
  3. extractionExtraction
  4. washthe extract is washed with saturated sodium chloride solution
  5. customdecanted
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f072f21a7d514c05b3f827370c5e58de
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Linked notes

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