Реакция #82212

Уравнение реакции

THF H2O

4-(chloromethyl)-2-(dimethylamino)thiazole

THF H2O

→

desired compound

2-(N,N-Dimethylamino)-4-(hydroxymethyl)thiazole

Условия реакции

Обработка

1. 1
   Фильтрацияthe mixture was filtered
2. 2
   Промывкаthe solid mass was washed with ethyl acetate
3. 3
   Концентрированиеthe combined filtrates were concentrated in vacuo
4. 4
   ДругоеThe black residue was purified by silica gel chromatography

Методика

A solution of 5.186 g (29 mmol) of 4-(chloromethyl)-2-(dimethylamino)thiazole in 100 ml of 1:1 THF/H2O was cooled to 0° C. and treated dropwise with a solution of 5.73 g (29 mmol) of silver tetrafluoroborate in 50 ml of 1:1 THF/H2O. After being stirred for 1 h, the mixture was filtered, the solid mass was washed with ethyl acetate, and the combined filtrates were concentrated in vacuo. The black residue was purified by silica gel chromatography to provide 0.80 g (17%) of the desired compound (Rf 0.24, 6% methanol in chloroform) as an oil. 1H NMR (CDCl3) δ 2.67 (br, 1 H), 3.09 (s, 6 H), 4.54 (s, 2 H), 6.35 (s, 1 H). Mass spectrum: (M+H)+ =159.

Источник