1,3-Dichloroacetone → 4-(Chloromethyl)-2-phenyl-1,3-thiazole

Beteiligte Stoffe

Reaktionsschritte

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with 2-(2-phenyl-thiazol-4-yl)-ethanol (prepared from thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a] to give 4-chloromethyl-2-phenyl-thiazole followed by side chain elongation in analogy to the sequence described in examples 13 a] to 13 d]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]2-ethoxy-3-{3-fluoro-4-[2-(2-phenyl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]2-ethoxy-3-{3-fluoro-4-[2-(2-phenyl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid as a light yellow gum.

Herkunft & Nachweise