Hydrochloric Acid → HCID 23679664, compound

HRID 1086368Notes

Reaction equation

HRID 1086368 reaction equation
[OH-].[Na+:2].[O:3]=[C:4]([CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][C:10]#[CH:11])[C:5]([OH:7])=[O:6].CI.Cl.O1CC[CH2:23][CH2:22]1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[O:3]=[C:4]([C:8]([CH2:22][CH3:23])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][C:10]#[CH:11])[C:5]([O-:7])=[O:6].[Na+:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 15024014HCID 15024014, compound

Product 1

HCID 23679664HCID 23679664, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

A 3N aqueous solution (0.61 ml) of sodium hydroxide and 2.0 ml of tetrahydrofuran were added to 0.15 g (0.71 mmole) of 2-oxo-3-phenyl-5-hexynoic acid, and the mixture was stirred until a completely uniform solution formed. Then, 0.091 ml (1.47 mmoles) of methyl iodide and 19 mg (0.083 mmole) of triethylbenzylammonium chloride were added, and the mixture was reacted at 40° C. for 16 hours. The reaction mixture was acidified with 1N hydrochloric acid, and extracted with ether. The ether layer was dried over magnesium sulfate. The drying reagent was separated by filtration, and the solvent was evaporated. The NMR spectral analysis of the resulting oily product led to the determination that 2-oxo-3-ethyl-3-phenyl-5-hexynoic acid formed in a yield of 62 %. Then, 0.35 ml of a 1N aqueous solution of sodium hydroxide was added, and the mixture was concentrated under reduced pressure. Ether was added, and the precipitated white solid was isolated by filtration to give 0.066 g (0.302 mmole) of sodium 2-oxo-3-ethyl-3-phenyl-5-hexynoate in a yield of 41 %.

Workup

  1. customformed
  2. customthe mixture was reacted at 40° C. for 16 hours
  3. extractionextracted with ether
  4. dry with materialThe ether layer was dried over magnesium sulfate
  5. customThe drying reagent was separated by filtration
  6. customthe solvent was evaporated
  7. customformed in a yield of 62 %
  8. concentrationthe mixture was concentrated under reduced pressure
  9. additionEther was added
  10. customthe precipitated white solid was isolated by filtration

Sources & evidence

ORD record
ord-4075c69257944bcabe1d3760b01a0047
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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