Sodium hydride → HCID 15381168, compound

HRID 2257061Notes

Reaction equation

HRID 2257061 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>C1COCC1>[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)[C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

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

Product 1

HCID 15381168HCID 15381168, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.8 g of sodium hydride as a 60% dispersion in oil are added in small portions at RT to a solution of 13.35 g of 3,4-dichlorophenylacetonitrile in 100 ml of THF and the reaction mixture is stirred for 3 hours at RT. It is cooled to -20° C., a solution of 16 g of 2-(3-bromopropoxy)tetrahydropyran in 30 ml of THF is added dropwise and the reaction mixture is stirred for 3 hours while the temperature is allowed to rise to RT. It is concentrated under vacuum, the residue is extracted with ether, the organic phase is washed with water, with a buffer solution of pH 4 and with water and dried over MgSo4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a toluene/AcOEt mixture (100/3; v/v) as the eluent to give 11 g of the expected product.

Workup

  1. temperatureIt is cooled to -20° C.
  2. stirringthe reaction mixture is stirred for 3 hours while the temperature
  3. customto rise to RT
  4. concentrationIt is concentrated under vacuum
  5. extractionthe residue is extracted with ether
  6. washthe organic phase is washed with water, with a buffer solution of pH 4 and with water
  7. customdried over MgSo4
  8. customthe solvent is evaporated off under vacuum
  9. customThe residue is chromatographed on silica using a toluene/AcOEt mixture (100/3; v/v) as the eluent

Sources & evidence

ORD record
ord-dd1c1df13403404fa80a69d36b0cedff
Source dataset
uspto-grants-1997_08
Patent number
US05656639

Reaction notes

Loading…