Reaction #47829

Reaction equation

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester

hydroxylamine hydrochloride

pyridine

→

titled compound

Yield 58.5%

1-hydroxyimino-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carboxylic Acid Ethyl Ester

Yield 58.5%

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturerefluxed for 1 hr
2. 2
   WashThe resulting mixture washed with saturated sodium bicarbonate
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe organic layer was separated
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Concentrationconcentrated under a reduced pressure
7. 7
   OtherThe resulting residue was purified by flash chromatography

Procedure

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester (1.5 g, 3.64 mmol) obtained in Example 7 was dissolved in ethanol (100 mL), hydroxylamine hydrochloride (759 mg, 10.92 mmol) and pyridine (1.15 g, 15.56 mmol) were added thereto, refluxed for 1 hr, and cooled to RT. The resulting mixture washed with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 0.91 g of the titled compound (yield: 58%).

Source