Sodium ethoxide → HCID 20193699, compound

HRID 2118414Notes

Reaction equation

HRID 2118414 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][C:10](=[O:22])[CH2:11][CH:12]([CH:19]([CH3:21])[CH3:20])[CH2:13][C:14]([O:16]CC)=O)[CH:4]=1.[O-]CC.[Na+]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH:9]2[C:10](=[O:22])[CH2:11][CH:12]([CH:19]([CH3:20])[CH3:21])[CH2:13][C:14]2=[O:16])[CH:4]=1

Participants

3

Reactant 2

HCID 2723922Sodium ethoxideHCID 20193713HCID 20193713, compound

Product 1

HCID 20193699HCID 20193699, compound

Procedure

The title compound was prepared from ethyl 6-(4-methoxy-2-pyridinyl)-3-(1-methylethyl)-5-oxohexanoate and ethanolic sodium ethoxide, refluxing for 2 hours according to the procedure of Example 2. The product separated from the aqueous phase as a yellow solid upon adjusting the pH to about 6 and was recovered by extraction with dichloromethane. Evaporation of the dried extract and recrystallization from acetonitrile gave the product as a white solid, mp 152°-154.5° C. The confirmatory elemental analysis is shown in Table II.

Workup

  1. temperaturerefluxing for 2 hours
  2. customThe product separated from the aqueous phase as a yellow solid
  3. customwas recovered by extraction with dichloromethane
  4. customEvaporation of the dried
  5. extractionextract
  6. customrecrystallization from acetonitrile

Sources & evidence

ORD record
ord-9c091834a8d043b58ef4a37d68745657
Source dataset
uspto-grants-1987_07
Patent number
US04678501

Reaction notes

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