反应详情

Combine (S)-N-methyl-N-(2-phenylpent-4-enyl)-2-methoxy-5-(4H-triazol-4-yl)benzamide (1.03 g, 2.74 mmol), acetone (15 mL, t-butanol (7.5 mL), water (7.5 mL), and a solution of N-methylmorpholine N-oxide (0.74 mL, 50% in water, 3.56 mmol). Add a solution of osmium tetraoxide (1.0 mL, 4% in water). After 36 hours, evaporate in vacuo to remove most of the acetone and extract the evaporated reaction mixture with dichloromethane. Extract the organic layer with an aqueous 10% solution of sodium thiosulfate. Extract the aqueous layer five times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give a residue. Combine the residue and tetrahydrofuran/water (20 mL, 4/1). Add sodium metaperiodate (0.7 g, 3.29 mmol). After 25 minutes, filter the reaction mixture, rinse the solids with tetrahydrofuran, and evaporate the filtrate to obtain a residue. Dilute the residue with dichloromethane (100 mL), extract with water, dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% methanol/dichloromethane to give the title compound.

1. customevaporate in vacuo
2. customto remove most of the acetone
3. extractionextract
4. customthe evaporated reaction mixture with dichloromethane
5. extractionExtract the organic layer with an aqueous 10% solution of sodium thiosulfate
6. extractionExtract the aqueous layer five times with dichloromethane
7. dry with materialDry the combined organic layers over Na2SO4
8. filtrationfilter
9. customevaporate in vacuo
10. customto give a residue
11. waitAfter 25 minutes
12. filtrationfilter the reaction mixture
13. washrinse the solids with tetrahydrofuran
14. customevaporate the filtrate
15. customto obtain a residue
16. extractionextract with water
17. dry with materialdry over MgSO4
18. filtrationfilter
19. customevaporate in vacuo
20. customto give a residue