Hydrochloric Acid → 7-[2-(3Oxo-5-phenyl-1-trans-pentenyl)-4-oxo-3-thiazolidinyl]heptanoic acid

HRID 867102Notes

Reaction equation

HRID 867102 reaction equation
[O:1]=[C:2]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3]P(=O)(OC)OC.[H-].[Na+].[CH:20]([CH:22]1[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:25](=[O:36])[CH2:24][S:23]1)=O.Cl>COCCOC.O>[O:1]=[C:2]([CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)/[CH:3]=[CH:20]/[CH:22]1[N:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:25](=[O:36])[CH2:24][S:23]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonateHCID 203174137-(2-Formyl-4-oxo-3-thiazolidinyl)heptanoic acid

Product 1

HCID 203173827-[2-(3Oxo-5-phenyl-1-trans-pentenyl)-4-oxo-3-thiazolidinyl]heptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dimethyl 2-oxo-4-phenylbutylphosphonate (1 molar equivalent) is added dropwise over a 1/2 hour period to a stirred suspension of sodium hydride (2equivalents) in 1,2-dimethoxyethane maintained at or below 20° C. To the resulting reaction mixture is slowly added 7-(2-formyl-4-oxo-3-thiazolidinyl)heptanoic acid (1 molar equivalent) with good stirring and cooling (sufficient to maintain a reaction temperature at or below 20° C.). Upon completing this addition, the reaction is stirred at ambient temperature for 1 hour, then heated at reflux for 1/2 hour, cooled to room temperature, and diluted with water. The aqueous mixture is acidified with dilute hydrochloric acid and extracted with ether. The organic extract is dried over sodium sulfate, filtered, and evaporated in vacuo at 40° C. leaving the title compound as an oily residue which is purified chromatographically on silica gel.

Workup

  1. temperaturemaintained at or below 20° C
  2. customTo the resulting reaction mixture
  3. temperaturecooling (sufficient
  4. temperatureto maintain a reaction temperature at or below 20° C.)
  5. additionthis addition
  6. stirringthe reaction is stirred at ambient temperature for 1 hour
  7. temperatureheated
  8. temperatureat reflux for 1/2 hour
  9. extractionextracted with ether
  10. extractionThe organic extract
  11. dry with materialis dried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo at 40° C.

Sources & evidence

ORD record
ord-4c58a194ec474416ac6760373e154f0f
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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