Sodium ethoxide → HCID 20193731, compound

HRID 2118412Notes

Reaction equation

HRID 2118412 reaction equation
[CH3:1][CH:2]([CH:4]([CH2:11][C:12](=[O:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:5][C:6]([O:8]CC)=O)[CH3:3].[O-]CC.[Na+]>CCOCC>[CH3:3][CH:2]([CH:4]1[CH2:5][C:6](=[O:8])[CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[C:12](=[O:20])[CH2:11]1)[CH3:1]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 20193715HCID 20193715, compound

Product 1

HCID 20193731HCID 20193731, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The subject compound was prepared from ethyl 3-(1-methylethyl)-6-(2-pyridinyl)-5-oxohexanoate and a sodium ethoxide solution according to the general procedure of Example 2, but employing a 2.83 hour reflux period following completion of the feed. On working up the reaction the ether-extracted aqueous phase was adjusted to pH 6 causing the product to separate as a tan solid which was extracted with ether, recovered by evaporation and recrystallized twice from cyclohexene to give a solid, mp 110°-112° C. The confirmatory elemental analysis is shown in Table II.

Workup

  1. temperaturereflux period
  2. extractionextracted aqueous phase
  3. customto separate as a tan solid which
  4. extractionwas extracted with ether
  5. customrecovered by evaporation
  6. customrecrystallized twice from cyclohexene
  7. customto give a solid, mp 110°-112° C

Sources & evidence

ORD record
ord-12dcc98899a54d1cbf5c0865302fa57a
Source dataset
uspto-grants-1987_07
Patent number
US04678501

Reaction notes

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