Ethyl 3-oxo-2-(2,5-dimethoxyphenylmethylidene)butanoate → Ethyl alpha-(2,5-dimethoxybenzyl)acetoacetate

HRID 726595Notes

Reaction equation

HRID 726595 reaction equation
[O:1]=[C:2]([CH3:20])[C:3](=[CH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[H][H]>[Pd].C(OCC)(=O)C>[O:1]=[C:2]([CH3:20])[CH:3]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 53919323Ethyl 3-oxo-2-(2,5-dimethoxyphenylmethylidene)butanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 12597482Ethyl alpha-(2,5-dimethoxybenzyl)acetoacetateYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 32.0 grams (0.126 mole) of ethyl 3-oxo-2-(2,5-dimethoxyphenylmethylidene)butanoate and 1.5 grams (catalyst) of 5% palladium on charcoal in 250 mL of ethyl acetate is hydrogenated using a Parr hydrogenation apparatus with hydrogen pressure at 20-40 psi. The hydrogenation requires about 12 hours. After this time, the reaction mixture is removed from the hydrogenator and filtered. The filtrate is concentrated under reduced pressure, yielding 32.2 grams of ethyl 3-oxo-2-(2,5-dimethoxy-phenylmethyl)butanoate. The NMR spectrum is consistent with the proposed structure.

Workup

  1. customAfter this time, the reaction mixture is removed from the hydrogenator
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c5d44cfade0f4c98a69622e4e64885d2
Source dataset
uspto-grants-1998_01
Patent number
US05710157

Reaction notes

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