Reaktion #1337939

Reaktionsgleichung

o-xylene dichloride

tetrahydrofuran

n-butyllithium

diisopropylamine

n-butyllithium

tetrahydrofuran

hydrochloric acid

lithiumdiisopropylamide

tetrahydrofuran

→

desired product

1,2-bis(indenyl)ethane

Lösungsmittel

hexane

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGby stirring at room temperature for 2 hours
3. 3
   TemperaturNext, the solution was cooled to −78° C.
4. 4
   workup.ADDITIONwas slowly added
5. 5
   workup.WAITAfter 30 minutes
6. 6
   ExtraktionThe solution was extracted with ethyl acetate
7. 7
   Trocknenthe collected organic layer was dried over anhydrous magnesium sulfate
8. 8
   EinengenAfter concentration
9. 9
   Extraktionunder reduced pressure, Soxhlet extraction

Vorschrift

1,4-bis(phenylsulfonyl)butane (16.9 g, 50.0 mmol) obtained in the above-mentioned (1) was dissolved in tetrahydrofuran (500 ml). After cooling to 0° C., 128 ml (n-butyllithium: 205 mmol) of a hexane solution having an n-butyllithium concentration of 1.6 mol/l was added. After 1 hour, a tetrahydrofuran solution (500 mol) of o-xylene dichloride (17.9 g, 102 mmol) was added to the solution which was being vigorously stirred, followed by stirring at room temperature for 2 hours. Next, the solution was cooled to −78° C., and a tetrahydrofuran solution (250 ml) of lithiumdiisopropylamide prepared from a hexane solution (256 ml) having an n-butyllithium concentration of 1.6 mol/l and diisopropylamine (57.7 ml) was slowly added thereto. After 30 minutes, 5% hydrochloric acid (200 ml) was added at 0C. The solution was extracted with ethyl acetate, and the collected organic layer was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, Soxhlet extraction using hexane was carried out to obtain a desired product. Its yield was 2.0 g, i.e., 15%.

Quelle