Ethyl ethoxyacetate → HCID 66635753, compound

HRID 872122Notes

Reaction equation

HRID 872122 reaction equation
[O-]CC.[Na+].[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.[CH2:15]([O:17][CH2:18][C:19](OCC)=[O:20])[CH3:16]>C(O)C>[CH2:15]([O:17][CH2:18][C:19](=[O:20])[CH:12]([C:9]1[CH:10]=[CH:11][C:6]([CH3:5])=[CH:7][CH:8]=1)[C:13]#[N:14])[CH3:16]

Participants

5

Reactant 3

HCID 69955Ethyl ethoxyacetateHCID 76280p-TolylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 66635753HCID 66635753, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide (2 eq) is dissolved in ethanol (200 mL) and 4-methylphenylacetonitrile (10.0) and ethyl ethoxyacetate (1.5 eq) are slowly added. The reaction mixture is stirred for 1 hour under reflux. Upon completion of the reaction, ethanol is removed under reduced pressure and water (100 mL) and ethyl acetate are added. The organic layer is removed and the aqueous layer is acidified by adding acetic acid (10 mL) and extracted 3 times with ethyl acetate. The extracted organic layer is collected, washed with water and dehydrated with MgSO4. After concentration under reduced pressure, the produced solid is recrystallized with Hx:EA=20:1 to obtain the target compound (70-95%).

Workup

  1. temperatureunder reflux
  2. customis removed under reduced pressure and water (100 mL) and ethyl acetate
  3. additionare added
  4. customThe organic layer is removed
  5. additionby adding acetic acid (10 mL)
  6. extractionextracted 3 times with ethyl acetate
  7. customThe extracted organic layer is collected
  8. washwashed with water
  9. concentrationAfter concentration under reduced pressure
  10. customthe produced solid is recrystallized with Hx

Sources & evidence

ORD record
ord-8b04516ad9b5491d82bb9a497690c325
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

Loading…