Hydrochloric Acid → 7-[2-(3-Hydroxy-5-phenyl-1-transpentenyl)-4-oxo-3-thiazolidinyl]heptanoic Acid

HRID 867103Notes

Reaction equation

HRID 867103 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[CH:5]=[CH:6]/[CH:7]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:10](=[O:21])[CH2:9][S:8]1.[H-].Cl>C(O)C>[OH:3][CH:4]([CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)/[CH:5]=[CH:6]/[CH:7]1[N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:10](=[O:21])[CH2:9][S:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 166653HydrideHCID 4311764Sodium borohydrideHCID 203173827-[2-(3Oxo-5-phenyl-1-trans-pentenyl)-4-oxo-3-thiazolidinyl]heptanoic acid

Product 1

HCID 203174237-[2-(3-Hydroxy-5-phenyl-1-transpentenyl)-4-oxo-3-thiazolidinyl]heptanoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.25 molar equivalents) is added in small portions over 1/2 hour to a stirred solution of 7-[2-(3-oxo-5-phenyl-1-trans-pentenyl)-4-oxo-3-thiazolidinyl]heptanoic acid (1 molar equivalent) in ethanol maintained at 0° to 5° C. Upon completing the hydride addition, the reaction mixture is stirred at 0° to 5° for 1/2 hour, then at ambient temperature for 21/2 hours. The resulting reaction mixture is cooled to 0° to 5° C., diluted with ice water and cautiously acidified to Congo Red with 2 N hydrochloric acid providing a turbid aqueous mixture which is extracted several times with ether. The combined organic extract is dried over sodium sulfate and filtered. In vacuo evaporation of the filtrate at 40° to 50° C. leaves an oily residue which is purified by chromatography on silica gel providing the title compound as a viscous, pale yellow oil.

Workup

  1. temperaturemaintained at 0° to 5° C
  2. customat ambient temperature
  3. custom2 hours
  4. customThe resulting reaction mixture
  5. temperatureis cooled to 0° to 5° C.
  6. extractionis extracted several times with ether
  7. extractionThe combined organic extract
  8. dry with materialis dried over sodium sulfate
  9. filtrationfiltered
  10. customIn vacuo evaporation of the filtrate at 40° to 50° C.
  11. customleaves an oily residue which
  12. customis purified by chromatography on silica gel providing the title compound as a viscous, pale yellow oil

Sources & evidence

ORD record
ord-f1e53d771c5a43c2883f6e586e3c21af
Source dataset
uspto-grants-1978_07
Patent number
US04102888

Reaction notes

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