Tetrahydrofuran → HCID 20288021, compound

HRID 126865Notes

Reaction equation

HRID 126865 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:19])[CH2:10]P(=O)(OCC)OCC)[CH:6]=[CH:7][CH:8]=1.O1CCCC1.[H-].[Na+].O=[C:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH2:29]1>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9](=[O:19])[CH2:10][C:28]2[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH2:30][CH:29]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 53666596HCID 53666596, compound

Product 1

HCID 20288021HCID 20288021, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

To a stirred mixture of 41 parts of diethyl [2-(3-methoxyphenyl)-2-oxoethyl]phosphonate and 180 parts of tetrahydrofuran are added portionwise 5 parts of sodium hydride dispersion 61% while cooling at about 15° C. Upon completion, stirring is continued for 30 minutes at room temperature. Then there are added dropwise 21 parts of ethyl 4-oxo-1-piperidinecarboxylate at about 20° C. Stirring is continued for 4 hours at 60° C. The reaction mixture is cooled, water is added and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is distilled, yielding 30 parts (83%) of ethyl 2,3-dihydro-4-[2-(3-methoxyphenyl)-2-oxoethyl]-1(6H)-pyridinecarboxylate; bp. 200°-210° C. at 1 mm. pressure.

Workup

  1. stirringStirring
  2. waitis continued for 4 hours at 60° C
  3. temperatureThe reaction mixture is cooled
  4. customthe layers are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. distillationThe residue is distilled

Sources & evidence

ORD record
ord-9a91ce810a6f4335986020b65d21134f
Source dataset
uspto-grants-1981_03
Patent number
US04254127

Reaction notes

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