Hydrochloric Acid → 4-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

HRID 1610686Notes

Reaction equation

HRID 1610686 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[K+].[C:26]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:27]C([O-])=O.[Cl-].[Mg+2].[Cl-].Cl>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6](=[O:8])[CH2:27][C:26]([O:32][CH2:33][CH3:34])=[O:31]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 983063-(2-Methylphenyl)prop-2-enoic acidHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

Product 1

HCID 202607254-Pentenoic acid, 5-(2-methylphenyl)-3-oxo-, eth

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methylcinnamic acid (50.71 g, 312.7 mmol) in tetrahydrofuran (500 ml) was added 1,1′-carbonyldiimidazole (55.8 g, 344 mmol) at room temperature, and the mixture was stirred as it was for 1 hr. To the mixture were added monoethyl malonate monopotassium salt (58.5 g, 344 mmol) and magnesium chloride (16.4 g, 172 mmol) at room temperature, and the mixture was stirred at 60° C. overnight. The reaction solution was diluted with ethyl acetate and water and acidified with conc. hydrochloric acid. The ethyl acetate layer was separated, and the aqueous layer was extracted with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1) to give the objective substance.

Workup

  1. stirringthe mixture was stirred at 60° C. overnight
  2. customThe ethyl acetate layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=9/1-6/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-81577f415a874644b6da42e31ccf19a2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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