Sodium ethoxide → HCID 21290659, compound

HRID 280694Notes

Reaction equation

HRID 280694 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:10][CH2:11][C:12]([O:14]CC)=O)=[CH:5][CH:4]=1.[O-]CC.[Na+]>C1(C)C(C)=CC=CC=1.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][C:12](=[O:14])[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 21290654HCID 21290654, compound

Product 1

HCID 21290659HCID 21290659, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

32.3 g of diethyl 3,3'-[(4-methoxyphenyl)-imino]dipropionate in 40 ml of xylene were added under argon to a freshly prepared solution of sodium ethoxide in absolute ethanol (2.3 g of sodium in 55 ml of ethanol). The mixture was heated slowly to about 110° C., by which means the ethanol was distilled off. Thereafter, the mixture was heated for a further 2 hours. The mixture was cooled to room temperature and poured on to ice. After neutralization with concentrated hydrochloric acid, the mixture was extracted with ether. The extract was washed three times with water, dried over sodium sulfate and evaporated. The product was chromatographed on silica gel with hexane/ethyl acetate (9:1) and yielded ethyl 1-(p-methoxyphenyl)-4-oxo-3-piperidinecarboxylate as a yellow oil.

Workup

  1. distillationwas distilled off
  2. temperatureThereafter, the mixture was heated for a further 2 hours
  3. temperatureThe mixture was cooled to room temperature
  4. additionpoured on to ice
  5. extractionAfter neutralization with concentrated hydrochloric acid, the mixture was extracted with ether
  6. washThe extract was washed three times with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe product was chromatographed on silica gel with hexane/ethyl acetate (9:1)

Sources & evidence

ORD record
ord-4857135db60748ad9dbc127ba957da13
Source dataset
uspto-grants-1986_05
Patent number
US04590270

Reaction notes

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