Reaktion #45871

Reaktionsgleichung

6-[3-(tert-Butyldimethylsiloxy)cyclopent-1-enyl]-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

tetra-n-butylammonium fluoride

ammonium chloride

→

compound

Ausbeute 46.0%

2-Cyclopropyl-7-fluoro-6-(3-hydroxycyclopent-1-enyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

Ausbeute 46.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at the same temperature for 5 minutes
2. 2
   ExtraktionThis was extracted three times with ethyl acetate
3. 3
   Waschenwashed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeThe insoluble matter was separated by filtration
6. 6
   Sonstigethe solvent was evaporated away
7. 7
   Sonstigethe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Vorschrift

6-[3-(tert-Butyldimethylsiloxy)cyclopent-1-enyl]-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-304) (275 mg, 0.67 mmol) was dissolved in tetrahydrofuran (6 ml), and at 0° C., tetra-n-butylammonium fluoride (1.0 M tetrahydrofuran solution, 1.0 ml, 1.0 mmol) was added. After stirring at room temperature under nitrogen atmosphere for 16 hours, aqueous saturated ammonium chloride solution was added to the solution at 0° C., followed by stirring at the same temperature for 5 minutes. This was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=1:1, v/v) to obtain the entitled compound (91 mg, 46%) as a white solid.

Quelle