Реакция #1605857

Уравнение реакции

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

Выход 89.2%

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

Выход 89.2%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

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

Методика

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 distilled off 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.

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