Ethyl Acetate → Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate

HRID 44203

Reaction equation

HRID 44203 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][NH:8][N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29](Cl)=[O:30])[CH3:18].C(OCC)(=O)C>C(#N)C.CCCCCC>[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29]([N:8]([CH3:7])[N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:30])[CH3:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 574373202,6-Diethyl-4-methylphenylacetyl chlorideHCID 73828661Ethyl 2-(methylhydrazono)propanoate

Product 1

HCID 76550641Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoateYield 49.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8058HexaneSolvent

Procedure

1.5 g of potassium carbonate was added to a solution of 2.0 g of ethyl 2-(methylhydrazono)propanoate in 35 mL of acetonitrile. The mixture was stirred under cooling with ice, to which a solution of 2.6 g of 2,6-diethyl-4-methylphenylacetyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes. The resulting mixture was further stirred for 3.5 hours at room temperature, and then concentrated under reduced pressure. To the residue obtained was added 20 mL of ice-water, which was extracted with ethyl acetate (20 mL×3). The extracts were combined, washed with a saturated sodium chloride aqueous solution (20 mL×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to basic alumina column chromatography (ethyl acetate:hexane=1:3 as eluent) to yield 1.9 g of the title compound as white crystals.

Workup

  1. additionwas added dropwise over about 20 minutes
  2. stirringThe resulting mixture was further stirred for 3.5 hours at room temperature
  3. concentrationconcentrated under reduced pressure
  4. customTo the residue obtained
  5. extractionwas extracted with ethyl acetate (20 mL×3)
  6. washwashed with a saturated sodium chloride aqueous solution (20 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained

Sources & evidence

ORD record
ord-386370daeb3c4bb9a6c03a4cd0dabdc2
Source dataset
uspto-grants-2013_09
Patent number
US08541414B2

Linked notes

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