反应详情

In this example, a mixture containing 4.0 gms (0.02 mol) of 5,5-dimethyl-3-hydroxy-2-propionylcyclohex-2-en-1-one and 3.6 gms (0.022 mol) of O-[(5-chlorothien-2-yl)methyl]hydroxylamine in 75 mls of ethanol was stirred at room temperature for about 12 hours. The mixture was then evaporated to remove the ethanol, affording a thick syrup. The syrup was then dissolved in methylene chloride and extracted twice with aqueous 5% wt. sodium hydroxide. The aqueous layer was separated and acidified with concentrated hydrochloric acid and then extracted twice with methylene chloride. The methylene chloride layer was separated, dried with magnesium sulfate, and filtered. The filtrate was evaporated under vacuum, affording a viscous liquid which was then purified via column chromatography eluting with tetrahydrofuran-hexane (1:2 vol. ratio) affording 4.8 gms of 2-{1-[(5-chlorothien-2-ylmethoxy)imino]propyl}-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one.

1. customThe mixture was then evaporated
2. customto remove the ethanol
3. customaffording a thick syrup
4. extractionextracted twice with aqueous 5% wt. sodium hydroxide
5. customThe aqueous layer was separated
6. extractionextracted twice with methylene chloride
7. customThe methylene chloride layer was separated
8. dry with materialdried with magnesium sulfate
9. filtrationfiltered
10. customThe filtrate was evaporated under vacuum
11. customaffording a viscous liquid which
12. customwas then purified via column chromatography
13. washeluting with tetrahydrofuran-hexane (1:2 vol. ratio)