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

HRID 1293558Notes

Reaction equation

HRID 1293558 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-aed5be7e4180485e9bf3dfe6c377ea45
Source dataset
uspto-grants-2007_07
Patent number
US07238812B2

Reaction notes

Loading…