Réaction #45633

Équation de réaction

trimethylsilyldiazomethane

7-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

tetrafluoroboric acid

water

trimethylsilyldiazomethane

→

compound

Rendement 79.0%

7-Fluoro-2-(2-methoxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Rendement 79.0%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas dropwise added
2. 2
   workup.STIRRINGby stirring at 0° C. for 1 hour
3. 3
   workup.ADDITIONwas added
4. 4
   Extractionfollowed by extraction with methylene
5. 5
   Lavagewashing with saturated brine
6. 6
   SéchageThe obtained organic layer was dried over anhydrous sodium sulfate
7. 7
   Autrethe solvent was evaporated away under reduced pressure
8. 8
   Lavageeluted with n-hexane/ethyl acetate (5:1

Mode opératoire

7-Fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-99) (50 mg, 0.15 mmol) was dissolved in methylene chloride (0.5 ml), aqueous 42% tetrafluoroboric acid solution (32 μl, 0.15 mmol) was added, then with cooling with ice, trimethylsilyldiazomethane (2 M hexane solution, 77 μl, 0.15 mmol) was dropwise added, followed by stirring at 0° C. for 10 minutes, further trimethylsilyldiazomethane (2 M, hexane solution, 77 μl, 0.15 mmol) was dropwise added, followed by stirring at 0° C. for 1 hour. After the reaction, water was added followed by extraction with methylene and washing with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative thin-layer silica gel column chromatography, eluted with n-hexane/ethyl acetate (5:1, v/v) to obtain the entitled compound (41.2 mg, 79%) as a colorless transparent oily substance.

Source