Реакция #450279

Уравнение реакции

hydrochloric acid

4-bromo-2-ethyl-6-methyl-1-[3-(4-trifluoromethoxyphenoxy)propyloxy]benzene

n-butyl lithium

triethoxy borane

→

3-ethyl-4-[3-(4-trifluoromethoxyphenoxy)propyloxy]-5-methylphenol

Выход 61.0%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGThen, the reaction mixture was stirred for 1 hour
3. 3
   Температураwhile warming to room temperature
4. 4
   workup.STIRRINGby stirring at room temperature for 20 minutes
5. 5
   ПромывкаThe tetrahydrofuran layer was washed with water
6. 6
   Сушкаdried with anhydrous magnesium sulfate
7. 7
   Концентрированиеconcentrated, to which 50 ml of toluene
8. 8
   workup.ADDITIONwas added
9. 9
   Температураthe mixture was heated at 70° C.
10. 10
    workup.STIRRINGunder stirring, to which 6 ml of 30% aqueous hydrogen peroxide solution
11. 11
    workup.ADDITIONwas added dropwise
12. 12
    ТемператураThe mixture was heated
13. 13
    Температураunder reflux for 1 hour
14. 14
    Промывкаwashed once with water, twice with 10% aqueous ammonium ferrous sulfate solution
15. 15
    СушкаThe toluene layer was dried with anhydrous magnesium sulfate
16. 16
    Концентрированиеconcentrated
17. 17
    Другоеto obtain a crude product

Методика

Then, 6.6 g of 4-bromo-2-ethyl-6-methyl-1-[3-(4-trifluoromethoxyphenoxy)propyloxy]benzene was dissolved in 200 ml of tetrahydrofuran, and the solution was stirred at -70° C., to which 9.6 ml of n-butyl lithium solution (in hexane, 1.58 mol/liter) was added dropwise, followed by further stirring at -70° C. for 2 hours. To this reaction mixture was added dropwise a solution of 2.2 g of triethoxy borane dissolved in 60 ml of tetrahydrofuran. Then, the reaction mixture was stirred for 1 hour, while warming to room temperature, and 13 ml of 10% aqueous hydrochloric acid solution was added in small portions, followed by stirring at room temperature for 20 minutes. The tetrahydrofuran layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated, to which 50 ml of toluene was added, and the mixture was heated at 70° C. under stirring, to which 6 ml of 30% aqueous hydrogen peroxide solution was added dropwise. The mixture was heated under reflux for 1 hour, and washed once with water, twice with 10% aqueous ammonium ferrous sulfate solution, and once with water. The toluene layer was dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 3.4 g of 3-ethyl-4-[3-(4-trifluoromethoxyphenoxy)propyloxy]-5-methylphenol (61% yield), nD25.4 1.4955.

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