Реакция #2286331

Уравнение реакции

2,6-dichloro-4-(2-hydroxy-ethyl)-phenol

2,6-Dichloro-4-(2-hydroxy-ethyl)-phenol

triethylamine

tert-butyl diphenylsilylchloride

→

4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol

Выход 60.4%

4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol

Выход 60.4%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

1. 1
   ПромывкаThe organics were washed with a 1N aqueous hydrochloric acid solution, water
2. 2
   Сушкаa saturated aqueous sodium chloride solution, dried with magnesium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated under vacuum

Методика

A solution of 2,6-dichloro-4-(2-hydroxy-ethyl)-phenol (16) (2.0 g, 9.66 mmol) in methylene chloride (20 mL) at 25° C. was treated with triethylamine (1.35 mL, 9.66 mmol) and tert-butyl diphenylsilylchloride (2.48 mL, 9.66 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with methylene chloride. The organics were washed with a 1N aqueous hydrochloric acid solution, water, and a saturated aqueous sodium chloride solution, dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 95:5 petroleum ether/ethyl acetate) afforded 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,6-dichloro-phenol (70) (2.60 g, 60%) as a pale yellow oil; HRMS m/e calcd for C24H26Cl2O2Si (M+Na)+ 467.0971, found 467.0977. Exact Mass=444.1079; Molecular Weight=445.47.

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