تفاعل #45633

معادلة التفاعل

trimethylsilyldiazomethane

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

tetrafluoroboric acid

water

trimethylsilyldiazomethane

→

compound

المردود 79.0%

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

المردود 79.0%

المذيبات

methylene chloride

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر