Water → HCID 66767035, compound

HRID 1662026Notes

Reaction equation

HRID 1662026 reaction equation
[C:1]1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=CC(=O)C)[CH:6]=CC=C[CH:2]=1.O=[C:25]([C:31]([O:33]CC)=O)[C:26]([O:28][CH2:29][CH3:30])=[O:27].Cl.[F:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][NH2:45])=[CH:40][CH:39]=1.O>C1COCC1.CCO.CCOC(C)=O>[F:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]2[C:31](=[O:33])[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:2][C:1]([CH3:6])=[N:45]2)=[CH:40][CH:39]=1

Participants

8

Reactant 4

HCID 962WaterHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 691051,3-Diethyl 2-oxopropanedioateHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 66767035HCID 66767035, compoundYield 43.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-triphenylphosphoranylidene-2-propanone (3.18 g, 9.99 mmol) in THF (50 mL) is added diethyl ketomalonate (1.74 g, 9.99 mmol). The resulting mixture is stirred at RT for 30 min to give a clear solution. Then this solution is added to a solution of 4-fluorophenylhydrazine hydrochloride (1.62 g, 9.96 mmol) in EtOH:H2O (30 mL:30 mL). After the resulting mixture is refluxed for 1 hour, TEA (3 mL) is added and the mixture is stirred at reflux for another 1 hour. Then it is concentrated and the residue is partitioned with saturated aqueous NH4Cl (30 mL) and EtOAc (30 mL). The organic phase is separated, dried and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (3:1) to give the product (1.20 g, 43% yield). MS (m/z): 277.1 (M+H).

Workup

  1. customto give a clear solution
  2. temperatureAfter the resulting mixture is refluxed for 1 hour
  3. stirringthe mixture is stirred
  4. temperatureat reflux for another 1 hour
  5. concentrationThen it is concentrated
  6. customthe residue is partitioned with saturated aqueous NH4Cl (30 mL) and EtOAc (30 mL)
  7. customThe organic phase is separated
  8. customdried
  9. concentrationconcentrated
  10. customThe residue is purified by silica gel column chromatography
  11. washeluting with PE

Sources & evidence

ORD record
ord-a8ee29b7c8f544d0b3c51f4d2a1a8501
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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