Trichloroacetic Acid → 5-(6-Bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester

HRID 977593Notes

Reaction equation

ClC(Cl)(Cl)C(O)=[O:4].[CH3:8][O:9][C:10](=[O:22])[CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[N:16]=1>CO.S(=O)(=O)(O)O.[Hg]=O>[CH3:8][O:9][C:10](=[O:22])[CH2:11][CH2:12][C:13](=[O:4])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[N:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 500 mg of red mercury oxide, 0.2 ml of boron trifluoride-diethyl ether complex and 10 mg of trichloroacetic acid in 1 ml of methanol is heated to 60° C. and a solution of 9.4 g of 5-(6-bromo-2-pyridyl)-4-pentynoic acid methyl ester in 15 ml 0f methanol is added to this catalyst solution at room temperature and the mixture is stirred for 2 hours at room temperature. Then, the reaction mixture is poured in 5% sulfuric acid, extracted with ethyl acetate, dried (Na2SO4) and concentrated by evaporation. 6.3 g of 5-(6-bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester is obtained as bright yellow oil.

Workup

extractionextracted with ethyl acetate
dry with materialdried (Na2SO4)
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-6846086519364f30983439de0a84bf9b
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05614634

Reaction notes

Loading…