Reaktion #45886

Reaktionsgleichung

6-acetyl-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Ethyl acetate

→

compound

Ausbeute 17.0%

2-Cyclopropyl-7-fluoro-6-isopropenyl-5-methyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 17.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONdiiodomethyl (320 μl, 3.97 mmol) was added to the suspension
2. 2
   SonstigeThe reaction liquid
3. 3
   Temperaturwas cooled to 0° C.
4. 4
   workup.STIRRINGby stirring at room temperature for 30 minutes
5. 5
   workup.WAITAfter 30 minutes
6. 6
   workup.ADDITIONwas dropwise added to the reaction liquid
7. 7
   workup.STIRRINGby stirring at room temperature for 30 minutes
8. 8
   Waschenby washing with 1 N hydrochloric acid and saturated brine
9. 9
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was evaporated away under reduced pressure
11. 11
    SonstigeThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate

Vorschrift

Under nitrogen atmosphere, zinc (520 mg, 0.79 mmol) was suspended in tetrahydrofuran (8 ml), then diiodomethyl (320 μl, 3.97 mmol) was added to the suspension, followed by stirring at room temperature for 30 minutes. The reaction liquid was cooled to 0° C. then titanium tetrachloride (794 μl 0794 mmol) was dropwise added, followed by stirring at room temperature for 30 minutes. After 30 minutes, 6-acetyl-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-82) (205 mg, 0-794 mmol) dissolved in tetrahydrofuran (2 ml) was dropwise added to the reaction liquid, followed by stirring at room temperature for 30 minutes. Ethyl acetate was added to the reaction liquid, followed by washing with 1 N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=4:1, v/v) to obtain the entitled compound (35 mg, 17%) as a white crystal.

Quelle