反应详情

温度

20 °C

To a mixed solution of 15 ml of a THF solution and 1.5 ml of tert-butanol containing 309 mg of potassium-butoxide was added slowly in a nitrogen stream at 0° C. 300 mg of the compound prepared in (7) above dissolved in 7.5 ml of THF. After stirring for 10 minutes at the same temperature, 0.22 ml of n-butyl nitrite was dropwise added to the mixture, followed by further stirring for 1.5 hours, during which the temperature was slowly raised to 20° C. The reaction mixture was adjusted to pH 1 with the addition of 1N hydrochloric acid, extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. To the residue obtained by evaporating the solvent-was added a mixture of 15 ml of acetic acid and 15 ml of acetic anhydride, and was added about 1 gm of zinc powder, followed by stirring at 20° C. for 18 hours. Insoluble substances were removed by filtration, the solvent was evaporated, and the residue was extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was subjected to silica gel column chromatography using a chloroform-methanol (97:3) mixed solvent as an eluant to obtain fractions containing the target compound. The fractions were concentrated to produce 311 mg of the title compound.

1. additionwas dropwise added to the mixture
2. extractionextracted with chloroform
3. washwashed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customTo the residue obtained
6. customby evaporating the solvent-was
7. additionadded
8. additiona mixture of 15 ml of acetic acid and 15 ml of acetic anhydride
9. additionwas added about 1 gm of zinc powder
10. stirringby stirring at 20° C. for 18 hours
11. customInsoluble substances were removed by filtration
12. customthe solvent was evaporated
13. extractionthe residue was extracted with chloroform
14. washThe extract was washed with saturated brine
15. dry with materialdried over anhydrous sodium sulfate
16. customAfter evaporating the solvent
17. additionmixed solvent as an eluant
18. customto obtain fractions
19. additioncontaining the target compound
20. concentrationThe fractions were concentrated