반응 #532291

반응 방정식

ammonium chloride

5-bromo-2-hydroxy-4-methylpyridine

sodium hydride

3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate

→

compound

수율 63.1%

4-(5-bromo-4-methylpyridin-2-yloxy)-2-methylbutan-2-ol

수율 63.1%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도cooling
3. 3
   기타the resultant reaction mixture
4. 4
   기타the resultant reaction mixture
5. 5
   workup.STIRRINGwas stirred at 60° C. for 4 hours
6. 6
   기타the resultant reaction mixture
7. 7
   추출was extracted with ethyl acetate
8. 8
   세척The organic phase was washed with saturated saline
9. 9
   건조was dried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONFrom the organic phase, the solvent was distilled off under reduced pressure
11. 11
    기타the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67)

실험 절차

To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), 5-bromo-2-hydroxy-4-methylpyridine (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60° C. for 4 hours. To the reaction mixture, a aqueous solution of saturated ammonium chloride was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a light yellow oil.

출처