反应详情

A solution of (4-hydroxyphenyl)propan-2-one ethylene ketal (1.4 g) in ethanol, was treated with a solution of sodium (0.16 g) in ethanol (25 ml) and heated under reflux for 10 minutes. A solution of 5-chloromethyl-2-(1,2,3,4-tetrahydropyran-2-yl)isoxazol-3-(2H)one (1.5 g) in ethanol was added dropwise, and the reaction was heated for 18 hr. The cooled solution was evaporated in vacuo, the residue partitioned between ethylacetate and water, the organic layer separated, dried (magnesium sulphate), and the solvent removed in vacuo to give an oil which was chromatographed on silica. Elution with ether: 60:80 petrol (1:1) gave an oil which was dissolved in acetone and treated with 2M hydrochloric acid solution (5 ml) and allowed to stand at room temperature for 4 hr. The solvent was removed in vacuo, the residue dissolved in ethyl acetate, washed with 1.2M sodium bicarbonate solution (1×50 ml), dried (magnesium sulphate , filtered and evaporated to give 5-(4-acetonylphenoxymethyl)3-hydroxyisoxazole.

1. temperatureheated
2. temperatureunder reflux for 10 minutes
3. temperaturethe reaction was heated for 18 hr
4. customThe cooled solution was evaporated in vacuo
5. customthe residue partitioned between ethylacetate and water
6. customthe organic layer separated
7. dry with materialdried (magnesium sulphate)
8. customthe solvent removed in vacuo
9. customto give an oil which
10. customwas chromatographed on silica
11. washElution with ether
12. custom60:80 petrol (1:1) gave an oil which
13. customThe solvent was removed in vacuo
14. dissolutionthe residue dissolved in ethyl acetate
15. washwashed with 1.2M sodium bicarbonate solution (1×50 ml)
16. dry with materialdried (magnesium sulphate
17. filtrationfiltered
18. customevaporated