반응 #82212

반응 방정식

THF H2O

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

THF H2O

→

desired compound

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

반응 조건

후처리

1. 1
   여과the mixture was filtered
2. 2
   세척the solid mass was washed with ethyl acetate
3. 3
   농축the combined filtrates were concentrated in vacuo
4. 4
   기타The black residue was purified by silica gel chromatography

실험 절차

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.

출처