Reaction #46164

Reaction equation

diisopropyl azodicarboxylate

hydroxyethylmorpholine

triphenyl phosphine

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide

→

6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide

Yield 99.0%

Solvents

benzene

tetrahydrofuran

Conditions

Workup

1. 1
   Otherwas adjusted to 0° C.
2. 2
   WashThe mixture was washed with brine
3. 3
   Extractionextracted with ethyl acetate
4. 4
   DryingThe separated organic layer was dried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated
6. 6
   Otherthe resulting residue was purified by column chromatography

Procedure

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (7.0 g, 22.78 mmol) was dissolved in tetrahydrofuran:benzene (150 ml:50 ml). Then, hydroxyethylmorpholine (3.59 g, 27.33 mmol) and triphenyl phosphine (7.17 g, 27.33 mmol) were added thereto. When the temperature was adjusted to 0° C., diisopropyl azodicarboxylate (5.53 g, 27.33 mmol) was added dropwise to the mixture followed by stirring for 2 hours at room temperature. The mixture was washed with brine and extracted with ethyl acetate. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 6-(2-morpholine-4-yl ethoxy)-1-oxo-3-phenyl-1H-indene-2-carboxylate isopropyl amide (9.5 g, yield 99%).

Source