Hydrochloric Acid → HCID 23679664, compound

HRID 1086365Notes

Reaction equation

HRID 1086365 reaction equation
[OH-].[Na+:2].[O:3]=[C:4]([CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:5]([O-:7])=[O:6].[Na+].[CH2:18](Br)[CH:19]=C.Cl.O1CCC[CH2:24]1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[O:3]=[C:4]([C:8]([CH2:18][CH3:19])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][C:10]#[CH:24])[C:5]([O-:7])=[O:6].[Na+:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 23679662HCID 23679662, compound

Product 1

HCID 23679664HCID 23679664, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

A 3N aqueous solution (0.76 ml) of sodium hydroxide and 3.0 ml of tetrahydrofuran were added to 0.30 g (1.39 mmoles) of sodium 2-oxo-3-phenylpentanoate, and the mixture was stirred until a completely uniform solution formed. Then, 0.24 ml (2.8 mmoles) of allyl bromide and 36 mg (0.16 mmole) of triethylbenzylammonium chloride were added, and the mixture reacted at room temperature for 25 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 80 %. Then, 1.3 ml of a 1N aqueous solution of sodium hydroxide was added to this product, and the mixture was concentrated under reduced pressure. Ether was added, and the precipitated white solid was isolated by filtration to give 0.086 g (0.34 mmole) of sodium 2-oxo-3-ethyl-3-phenyl-5-hexynoate formed in a yield of 24 %.

Workup

  1. customformed
  2. customthe mixture reacted at room temperature for 25 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 80 %
  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-7c31f90a98ba4f45bf18edcdbd5fa40e
Source dataset
uspto-grants-1991_07
Patent number
US05028738

Reaction notes

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