반응 #3051

반응 방정식

magnesium

title compound

5-[[3-(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-thiazolidinone

Magnesium

ethyl acetate

magnesium

→

title compound

수율 72.9%

5-[[3-(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-4-thiazolidinone

수율 72.9%

용매

methanol

반응 조건

후처리

1. 1
   기타the resulting reaction mixture
2. 2
   workup.WAITAfter 3 hours
3. 3
   workup.ADDITIONwere added
4. 4
   workup.STIRRINGStirring of the reaction solution at room temperature
5. 5
   workup.WAITcontinued overnight
6. 6
   기타By the next morning a yellow precipitate had formed
7. 7
   workup.DISSOLUTIONThis precipitate was dissolved
8. 8
   기타The organic layer from the resulting two-phase mixture was isolated
9. 9
   건조dried over sodium sulfate
10. 10
    기타The volatile components of the organic layer were removed
11. 11
    workup.DISSOLUTIONThe residue was then dissolved in 25 ml of methylene chloride
12. 12
    기타the resulting solution was chromatographed on a silica gel chromatography column
13. 13
    workup.ADDITIONas containing essentially pure product
14. 14
    기타were evaporated

실험 절차

A portion of the title compound from Example 77 (395.1 mg; 1.5 mmol) was dissolved in 9 ml of methanol. Magnesium (72.9 mg; 3.0 mmol) was then added to the solution and the resulting reaction mixture was stirred at room temperature for 3 hours. After 3 hours, most of the magnesium which had been added originally appeared to be gone so an additional 182.3 mg (7.5 mmol) of magnesium were added. Stirring of the reaction solution at room temperature continued overnight. By the next morning a yellow precipitate had formed. This precipitate was dissolved by adding the methanolic reaction solution to an ethyl acetate/1N hydrochloric acid mixture. The organic layer from the resulting two-phase mixture was isolated and then dried over sodium sulfate. The volatile components of the organic layer were removed and the resulting residue was chased with methylene chloride. The residue was then dissolved in 25 ml of methylene chloride and the resulting solution was chromatographed on a silica gel chromatography column using a 5-20% isopropyl alcohol in hexanes gradient. Those fractions identified as containing essentially pure product were evaporated to provide 0.29 g of title compound. m.p. 65°-70° C.

출처