Reaktion #157681

Reaktionsgleichung

Water

tetrabutylammonium fluoride

(4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)(5-chloro-6-methoxypyridin-2-yl)methanone

→

title compound

Ausbeute 93.0%

(5-Chloro-6-methoxypyridin-2-yl)[3-chloro-4-(propan-2-yloxy)phenyl]methanone

Ausbeute 93.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenafter which the filtrate was concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting residue was dissolved in N,N-dimethylformamide (10 mL)
7. 7
   workup.ADDITION2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature
8. 8
   workup.STIRRINGby stirring at 65° C. for three hours
9. 9
   Sonstigewas returned to room temperature
10. 10
    workup.ADDITIONwater was added
11. 11
    Extraktionfollowed by extraction with ethyl acetate
12. 12
    TrocknenThe organic layer was dried over anhydrous magnesium sulfate
13. 13
    Filtrationfiltered
14. 14
    SonstigeThe solvent was then evaporated under reduced pressure
15. 15
    SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Vorschrift

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (3.39 mL) was added to a solution of (4-{[tert-butyl(dimethyl)silyl]oxy}-3-chlorophenyl)(5-chloro-6-methoxypyridin-2-yl)methanone (700 mg) in tetrahydrofuran (10 mL) at room temperature, and the mixture was stirred at room temperature for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in N,N-dimethylformamide (10 mL), and 2-iodopropane (333 μL) and potassium carbonate (464 mg) were sequentially added at room temperature, followed by stirring at 65° C. for three hours. The reaction solution was returned to room temperature and water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to give the title compound as a colorless oil (538 mg, 93%).

Quelle