Ethyl Acetoacetate → Ethyl α-acetyl-4-methoxybenzenepropanoate

HRID 1421254Notes

Reaction equation

HRID 1421254 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.N12CCCN=C1CCCCC2>CC#N>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([CH2:16][C:15]1[CH:18]=[CH:19][C:12]([O:11][CH3:10])=[CH:13][CH:14]=1)[C:3](=[O:4])[CH3:5])[CH3:9]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 699934-Methyloxybenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 12248936Ethyl α-acetyl-4-methoxybenzenepropanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl acetoacetate and 4-methoxybenzyl chloride is stirred under an argon atmosphere with 1,8-diazabicyclo[5.4.0]undec-7-ene at room temperature in CH3CN. The mixture is partitioned between 3 N HCl and EtOAc. The organic extract is washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl and dried (Na2SO4). The solvent is removed in vacuo to afford the title compound.

Workup

  1. customThe mixture is partitioned between 3 N HCl and EtOAc
  2. extractionThe organic extract
  3. washis washed successively with H2O, aqueous NaHCO3, H2O and saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2e56d6cfdea142a6a9c8557bf84d89fb
Source dataset
uspto-grants-2000_06
Patent number
US06075037

Reaction notes

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