Malononitrile → 4-Benzyloxybenzoylmalononitrile

HRID 1822741Notes

Reaction equation

HRID 1822741 reaction equation
C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C.[CH2:18]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:35](#[N:39])[CH2:36][C:37]#[N:38]>CN(C=O)C>[CH2:18]([O:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([CH:36]([C:35]#[N:39])[C:37]#[N:38])=[O:32])=[CH:33][CH:34]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8471TriethylamineHCID 738804-(Benzyloxy)benzoic acidHCID 76257Diethyl cyanophosphonate

Product 1

HCID 221697854-Benzyloxybenzoylmalononitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Diethylcyanophosphonate (5 mmol) and triethylamine (15 mmol) are added to a solution of 4-benzyloxybenzoic acid (18, 5 mmol) and malononitrile (4.8 mmol) in DMF (10 mL) stirred at 0° C. After the addition is complete, stirring is continued as the solution is allowed to warm to ambient temperature. Progress of the reaction is followed by tlc and when complete, the reaction solution is concentrated under reduced pressure. The residue is taken up in EtOAc and washed with cold 1N HCl and then with aq. NaHCO3. The alkaline bicarbonate wash is acidified with 6N HCl and the mixture is extracted with EtOAc. The combined EtOAc extract solutions are dried (Na2SO4), filtered and concentrated under reduced pressure, giving the desired 4-benzyloxybenzoylmalononitrile 19. The product is used in the next step without further purification.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. temperatureto warm to ambient temperature
  4. concentrationthe reaction solution is concentrated under reduced pressure
  5. washwashed with cold 1N HCl
  6. washThe alkaline bicarbonate wash
  7. extractionthe mixture is extracted with EtOAc
  8. extractionThe combined EtOAc extract solutions
  9. dry with materialare dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7e957fdea184609968bfa72eb6b8357
Source dataset
uspto-grants-2006_05
Patent number
US07037912B2

Reaction notes

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