Triethylamine → Methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butynoate

HRID 1794686Notes

Reaction equation

HRID 1794686 reaction equation
C(N(CC)CC)C.Br[CH:9]([CH:14](Br)[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)=[O:16])[C:10]([O:12][CH3:13])=[O:11]>C(Cl)Cl>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([C:15](=[O:16])[C:14]#[C:9][C:10]([O:12][CH3:13])=[O:11])[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 22222623Methyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate

Product 1

HCID 22222579Methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butynoateYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triethylamine (27 mg) in methylene chloride (0.5 ml) was added to a solution of methyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate (49 mg, 0.1 mmol), prepared above, in methylene chloride (0.5 ml). The mixture was stirred at room temperature for 15 min and then heated under reflux with stirring for 2 hr. The mixture was then treated by a conventional method, and the crude product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give the title compound as a yellow crystal (21 mg, 71%).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. stirringwith stirring for 2 hr
  4. additionThe mixture was then treated by a conventional method
  5. customthe crude product was purified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-41389cf86889494ea10c4a9a940cd964
Source dataset
uspto-grants-2006_04
Patent number
US07022860B2

Reaction notes

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