광학활성 제초제 fenoxaprop-p-ethyl [ethyl (R)-2-{4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate]의 새로운 합성법

Fenoxaprop-p-ethyl[Ethyl (R)-2-{4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate] is well known as a herbicide for its specific activity against the weed grasses. This compound was synthesized by the reaction of 4-(6-chloro-1,3-benzoxazol-2-yloxy)phenol and ethyl (S)-O-(p-toluenesulfonyl)lactate in good yields with high optical pure(optical purity: 99.9% up). In this process Walden inversion occurs, whereby the S-configuration of the propionic acid derivative is converted to the R-configuration of the final product. 4-(6-Chloro-l,3-benzoxazol-2-yloxy)phenol was obtained by 5 step reactions in over-all 70% yields using inexpensive raw materials. 화본과 제초제의 대표적인 화합물인 광학활성 fenoxaprop-p-ethyl[ethyl(R)-2-{4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy}propionate]을 4-(6-chloro-1,3-benzoxazol-2-yloxy)phenol과 ethyl (S)-O-(p-toluenesulfonyl)lactate의 치환반응(Walden Inversion)을 이용하여 90%의 수율(광학활성순도 : 99.9% 이상)로 얻었다. 4-(6-chloro-1,3-benzoxazol-2-yloxy)phenol은 기초적인 원료인 아미노페놀, 우레아, 클로린, 유황 등을 자일렌, 메탄올, 디클로로에탄 등의 용매를 사용하여 6단계의 반응을 거처 70% 의 수율로 합성하였다.