Acetonitrile → HCID 10858248, Verbindung

To a solution of 1,1,1,3,3,3-hexamethyldisilazane (2.19 g, 13.6 mmol.) in tetrahydrofuran (80 ml) was gradually added dropwise, under argon atmosphere at -78° C., a normal butyl lithium hexane solution (1.56 M, 8.72 ml, 13.6 mmol.). The mixture was stirred for 10 minutes, to which was then added dropwise acetonitrile (0.65 ml, 12.4 mmol.). The mixture was stirred for further 20 minutes, to which was added dropwise a solution of 6-methoxy-2-phenyl-1-indanone (2.70 g, 11.3 mmol.) in tetrahydrofuran (10 ml), and the mixture was stirred for one hour. The temperature of the reaction mixture was gradually reverted to room temperature while pouring water thereto, and the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was dissolved in toluene (100 ml), to which was added 10-camphor-sulfonic acid (0.5 g). The reaction mixture was heated for 2 hours under reflux. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, and the organic substance was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue thus obtained was recrystallized to afford the titled compound (yield 0.47 g, yield 16%).

1. stirringThe mixture was stirred for further 20 minutes, to which
2. stirringthe mixture was stirred for one hour
3. customwas gradually reverted to room temperature
4. extractionthe organic substance was extracted with ethyl acetate
5. washThe extract solution was washed with a saturated aqueous saline solution and water
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationby distilling off the solvent under reduced pressure
8. dissolutionThe residue was dissolved in toluene (100 ml), to which
9. additionwas added 10-camphor-sulfonic acid (0.5 g)
10. temperatureThe reaction mixture was heated for 2 hours
11. temperatureunder reflux
12. additionThe reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate
13. extractionthe organic substance was extracted with ethyl acetate
14. washThe extract solution was washed with a saturated aqueous saline solution and water
15. dry with materialdried over anhydrous magnesium sulfate
16. distillationthe solvent was distilled off under reduced pressure
17. customThe residue thus obtained
18. customwas recrystallized

ORD-Eintrag

ord-0941d6f91b6c4343bf964832f302470d

Quelldatensatz

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05922771