Reaction #1106642

Reaction equation

NaOH

1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(6-methoxypyridin-3-yl)propan-1-one

TFA

→

white solid

Yield 35.8%

2,4-dihydroxyphenyl-3-(6-methoxypyridin-3-yl)propan-1-one

Yield 35.8%

Solvents

CH3CN

Conditions

Workup

1. 1
   ExtractionThe aqueous was extracted with 100 ml EtOAc
2. 2
   WashThe organic layer was washed with brine
3. 3
   Dryingdried (Na2SO4)
4. 4
   Concentrationconcentrated
5. 5
   OtherThe residue was purified by silica gel chromatography (15% EtOAc/Hexane)

Procedure

To a solution of 1-(2-hydroxy-4-(methoxymethoxy)phenyl)-3-(6-methoxypyridin-3-yl)propan-1-one (1.62 g, 5.11 mmol) in CH3CN (30 ml) at room temperature was added TFA (2 ml) dropwise, two drops of water. The reaction was stirred at same temperature for 8 h. Aqueous 1N NaOH was added to the reaction mixture until pH=7. The aqueous was extracted with 100 ml EtOAc, and the organic layers were combined. The organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (15% EtOAc/Hexane) to provide 0.5 g (35%) of white solid.

Source