Hydrochloric Acid → HCID 13373522, compound

HRID 358479Notes

Reaction equation

HRID 358479 reaction equation
[H-].[Na+].[CH:3]([O:5][CH2:6][CH3:7])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][CH2:16][C:17](OCC)=[O:18])[CH:9]=1.Cl>CN(C)C=O>[CH:17]([CH:16]([CH2:15][CH2:14][C:10]1[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 116799753-Pyridinebutanoic acid, ethyl ester

Product 1

HCID 13373522HCID 13373522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2.53 g. of sodium hydride in 35 ml. of anhydrous dimethyl formamide was prepared. The suspension was cooled to about 0° C. with stirring. Next, a mixture of 9.56 g. of ethyl formate and 19 g. of ethyl 4-(3-pyridyl)butyrate were added. The consequent reaction mixture was stirred at about 0° C. for 1 additional hour and then at room temperature for about 3 days. The reaction mixture was acidified with 2N aqueous hydrochloric acid and the acidic aqueous solution evaporated to a very small volume in vacuo. The acidity of the solution was adjusted to pH=6 by the addition of solid potassium carbonate. The neutral aqueous layer was then extracted with ether. The ether layer was separated and dried. Evaporation of the ether yielded 16.4 g. of ethyl 2-formyl-4-(3-pyridyl)butyrate (formed in the above reaction) as an orange oil.

Workup

  1. additionA suspension of 2.53 g
  2. additionNext, a mixture of 9.56 g
  3. customThe consequent reaction mixture
  4. stirringwas stirred at about 0° C. for 1 additional hour
  5. customthe acidic aqueous solution evaporated to a very small volume in vacuo
  6. additionThe acidity of the solution was adjusted to pH=6 by the addition of solid potassium carbonate
  7. extractionThe neutral aqueous layer was then extracted with ether
  8. customThe ether layer was separated
  9. customdried
  10. customEvaporation of the ether
  11. customyielded 16.4 g

Sources & evidence

ORD record
ord-5f89918373ff4aaf9f5f5c61206f441e
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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