Sodium hydride → HCID 21699575, compound

HRID 1955051Notes

Reaction equation

HRID 1955051 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][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.[Cl-].[NH4+]>C1COCC1.O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:12][NH2:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

7

Reactant 4

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

Product 1

HCID 21699575HCID 21699575, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

15 g of sodium hydride at 60% in oil are suspended in 200 ml of anhydrous THF. A solution of 69.5 g of 3,4-dichlorophenylacetonitrile in 500 ml of THF is added dropwise over 30 minutes and then the reaction mixture is stirred at RT for 1 hour. The mixture is cooled to -20° C. and a solution of 85 g of 1-bromo-3-(tetrahydropyran-2-yloxy)propane in 100 ml of THF is added. The mixture is allowed to return to RT and after 2 hours it is poured over a solution of 50 g of ammonium chloride in 3 liters of water. The mixture is extracted with ether, washed with a saturated solution of sodium chloride, decanted, dried over MgSO4 and concentrated. The residue is chromatographed on silica gel, eluting with a mixture of toluene and an AcOEt gradient (3 to 5%). The pure product fractions are concentrated to give 77 g of expected product in the form of an oil.

Workup

  1. temperatureThe mixture is cooled to -20° C.
  2. waitto return to RT and after 2 hours
  3. extractionThe mixture is extracted with ether
  4. washwashed with a saturated solution of sodium chloride
  5. customdecanted
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel
  9. washeluting with a mixture of toluene
  10. concentrationThe pure product fractions are concentrated

Sources & evidence

ORD record
ord-044c1817bcfd4ab6b2815bbba5c667ec
Source dataset
uspto-grants-2000_09
Patent number
US06124316

Reaction notes

Loading…