Реакция #46153

Уравнение реакции

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester

3-phenylpropanol

triphenylphosphine

Diethyl azodicarboxylate

→

title compound

Выход 85.0%

3-phenyl-6-(3-phenylpropyloxy)-1-oxo-1H-indene-2-carboxylate ethyl ester

Выход 85.0%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Другоеat 0° C
3. 3
   Промывкаthe mixture was washed with brine
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   Сушкаthe extract was dried over anhydrous magnesium sulfate
6. 6
   Концентрированиеthe concentrated under a reduced pressure
7. 7
   Другоеthe residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10)

Методика

6-Hydroxy-1-oxo-3-phenyl-1H-indene-2-carboxylate ethyl ester (1.7 g, 6.07 mmol), 3-phenylpropanol (1.65 g, 12.14 mmol) and triphenylphosphine (3.18 g, 12.14 mmol) were dissolved in tetrahydrofuran (100 ml). Diethyl azodicarboxylate (2 ml, 12.14 mmol) dissolved in tetrahydrofuran (20 ml) was added dropwise thereto at 0° C. After stirring for 6 hours at room temperature, the mixture was washed with brine, extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate, the concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (diethyl ether:hexane=1:10) to obtain the title compound (yield 85%) as a dark red solid.

Источник