Triethylamine → Ethyl 4-(3,4-Dimethoxyphenyl)-4-oxo-2-butynoate

HRID 1794687Notes

Reaction equation

HRID 1794687 reaction equation
Br[CH:2]([CH:8](Br)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=[O:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.COC1C=C(C(=O)C#CC(OC)=O)C=CC=1OC>C(Cl)Cl>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([C:9](=[O:10])[C:8]#[C:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:16]=[CH:15][C:14]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22222579Methyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butynoateHCID 22222634Ethyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate

Product 1

HCID 22222587Ethyl 4-(3,4-Dimethoxyphenyl)-4-oxo-2-butynoateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl 2,3-dibromo-4-(3,4-dimethoxyphenyl)-4-oxobutanoate (4.76 g, 11.2 mmol), prepared above, in methylene chloride (20 ml) and a solution of triethylamine (4 g) in methylene chloride (5 ml) were subjected to reaction and treatment in the same manner as described above in connection with Intermediate 1. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate) to give the title compound (2.4 g, 82%) as a yellow crystal.

Workup

  1. customThe crude product was purified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fee8d5246e034db2bf8e06eee28859ba
Source dataset
uspto-grants-2006_04
Patent number
US07022860B2

Reaction notes

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