Реакция #494376

Уравнение реакции

(2-chloropyridin-4-yl)methanol

tert-butyldimethylchlorosilane

imidazole

→

4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine

Растворители

DMF

water

Условия реакции

Обработка

1. 1
   Промывкаwashed 3× with water
2. 2
   Сушкаdried over sodium sulfate
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   Промывкаeluting with 0-15% EtOAc in hexanes

Методика

To a solution of (2-chloropyridin-4-yl)methanol (0.307 g, 2.14 mmol) in 20 mL of DMF at 0° C. under an atmosphere of nitrogen was added tert-butyldimethylchlorosilane (0.355 g, 2.35 mol) and imidazole (0.160 g, 2.35 mmol). After 1 h, the mixture was diluted with water, washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The resultant residue was subjected to silica gel chromatography eluting with 0-15% EtOAc in hexanes to provide 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloropyridine that gave a mass ion (ES+) of 258.1 for [M+H]+.

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