Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate → (2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

反応式

[Cl:1][C:2]1[S:3][C:4]([C:11](OCC)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.C([BH3-])#N.[Na+].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

参加物

実験手順

To a mixture of 2.6 g (0.01 mol) of ethyl 2-chloro-4-(trifluoromethyl)-5-thiazolecarboxylate and 10 ml of ethanol was added. 0.62 g of sodium cyanoborohydride. The reaction mixture was stirred for 5 minutes and 0.40 g of sodium borohydride was added. The temperature of the reaction mixture raised spontaneously to boiling point. The reaction mixture was stirred for 30 minutes and quenched with water. The aqueous mixture was extracted with ether. The ether solution was dried over CaSO4 and concentrated under reduced pressure. The residue was crystallized from petroleum ether to give 1.6 g (74%) of 2-chloro-4-(trifluoromethyl)-5-thiazolemethanol, mp 39°-45° C.