Sodium hydride → HCID 22314814, compound

HRID 966412Notes

Reaction equation

HRID 966412 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[CH3:10].Br[CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1>C1COCC1>[CH3:3][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[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 764012-(3,4-Dimethylphenyl)acetonitrileHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Product 1

HCID 22314814HCID 22314814, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.6 g of 60% sodium hydride in oil are added portionwise at RT to a solution of 20 g of 3,4-dimethylphenylacetonitrile in 100 ml of anhydrous THF, and the mixture is left stirring at RT for 2 hours. 29 g of 1-bromo-2-(2-tetrahydropyranyloxy)ethane are then added dropwise and the mixture is left stirring at RT for 2 days. The reaction mixture is poured onto ice and extracted with EtOAc, the organic phase is washed with water and with saturated NaCl solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with toluene and then with a gradient of a toluene/EtOAc mixture from (99/1; v/v) to (90/10; v/v). 17 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring at RT for 2 days
  4. additionThe reaction mixture is poured onto ice
  5. extractionextracted with EtOAc
  6. washthe organic phase is washed with water and with saturated NaCl solution
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated off under vacuum
  9. customThe residue is chromatographed on silica gel
  10. washeluting with toluene

Sources & evidence

ORD record
ord-68bfd2c395864c06bc29e7fc5939e605
Source dataset
uspto-grants-2005_10
Patent number
US06951940B2

Reaction notes

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