Sodium hydride → HCID 18928670, compound

HRID 1599470Notes

Reaction equation

HRID 1599470 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].[H-].[Na+].[C:18]([N:26]1[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[C:18]([N:26]1[CH2:31][CH2:30][C:29](=[C:6]([CH3:7])[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:28][CH2:27]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 90583N-Benzoyl-4-piperidoneHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 18928670HCID 18928670, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of triethyl 2-phosphonopropionate (50.0 g) in dry tetrahydrofuran (75 ml) was added dropwise to a stirred suspension of sodium hydride (60% in mineral oil, 8.0 g) in dry tetrahydrofuran (275 ml) under nitrogen and stirred at 20° C. for 10 minutes until a clear solution was formed. 1-Benzoyl-4-piperidone (34.5 g) in dry tetrahydrofuran (75 ml) was added dropwise to the clear solution and the reaction mixture heated under reflux for 16 hours. After quenching the reaction mixture with 5M hydrochloric acid (20 ml), the resulting solid was removed by filtration. Excess ether was added to the filtrate, the aqueous layer separated off and the ethereal layer washed (water), dried, filtered and concentrated to give ethyl 2-(1-benzoyl-4-piperidylidene)propionate as an oil.

Workup

  1. customwas formed
  2. temperaturethe reaction mixture heated
  3. temperatureunder reflux for 16 hours
  4. customAfter quenching the reaction mixture with 5M hydrochloric acid (20 ml)
  5. customthe resulting solid was removed by filtration
  6. additionExcess ether was added to the filtrate
  7. customthe aqueous layer separated off
  8. washthe ethereal layer washed (water)
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c050f79e8c194d3c99def682c54fdb67
Source dataset
uspto-grants-1998_04
Patent number
US05741800

Reaction notes

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