반응 #663848

반응 방정식

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

ammonium chloride

sodium hydride

5-bromo-2-hydroxy-6-methylpyridine

3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate

Sodium hydride

→

title compound

수율 89.2%

4-(5-bromo-6-methylpyridin-2-yloxy)-2-methylbutan-2-ol

수율 89.2%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   온도cooling
2. 2
   기타the resultant reaction mixture
3. 3
   기타the resultant reaction mixture
4. 4
   workup.STIRRINGwas stirred at 60° C. for 1.5 hours
5. 5
   workup.ADDITIONwas further added
6. 6
   추출the mixture was extracted with ethyl acetate
7. 7
   세척The organic phase was washed with brine
8. 8
   건조dried over anhydrous sodium sulfate
9. 9
   기타From the organic phase, the solvent was removed by evaporation under reduced pressure
10. 10
    기타the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=50:50 to 33:67)

실험 절차

To a suspension of sodium hydride (containing about 40% of a mineral oil, 0.38 g) in N,N-dimethylformamide (10 mL), 5-bromo-2-hydroxy-6-methylpyridine (1.00 g) and 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (1.51 g) were added under ice-cooling and the resultant reaction mixture was stirred at 60° C. for 2.5 hours. To the mixture, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (0.50 g) was further added and the resultant reaction mixture was stirred at 60° C. for 1.5 hours. Sodium hydride (containing about 40% of a mineral oil, 40 mg) was further added. To the reaction mixture, a saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and then dried over anhydrous sodium sulfate. From the organic phase, the solvent was removed by evaporation under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=50:50 to 33:67) to give the title compound (1.3 g) as a pale yellow oil.

출처