Réaction #82212

Équation de réaction

THF H2O

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

THF H2O

→

desired compound

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

Conditions de réaction

Traitement

1. 1
   Filtrationthe mixture was filtered
2. 2
   Lavagethe solid mass was washed with ethyl acetate
3. 3
   Concentrationthe combined filtrates were concentrated in vacuo
4. 4
   AutreThe black residue was purified by silica gel chromatography

Mode opératoire

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.

Source