反应详情

To 5 g (0.0163 mol) of 2-propionyl-3-hydroxy-5-(4-methylthiophenyl)cyclohex-2-en-1-one in a flask cooled to in an ice-water bath was added 25 mL (0.177 mol) of trifluoroacetic anhydride dropwise over 5 minutes. The ice-water bath was removed and the solution stirred at ambient temperature for 3 hours. The solvent was removed in vacuo and the oil remaining was dissolved in 82 mL of 1N NaOH and the solution stirred at ambient temperature overnight. The mixture was diluted with 1200 mL of water, filtered and the filtrate acidified with 5 mL of concentrated HCl with the product precipitating as an oily solid. The product was dissolved in 150 mL of methylene chloride and the solution washed twice with 150 mL portions of water and dried over Na2SO4. Removal of the solvent in vacuo gave the above named product in a yield of 4.0 g (88.7 percent of theoretical).

1. customThe ice-water bath was removed
2. customThe solvent was removed in vacuo
3. dissolutionthe oil remaining was dissolved in 82 mL of 1N NaOH
4. stirringthe solution stirred at ambient temperature overnight
5. additionThe mixture was diluted with 1200 mL of water
6. filtrationfiltered
7. customprecipitating as an oily solid
8. dissolutionThe product was dissolved in 150 mL of methylene chloride
9. washthe solution washed twice with 150 mL portions of water
10. dry with materialdried over Na2SO4
11. customRemoval of the solvent in vacuo
12. customgave the