合成路线:The cyclization of 3-methoxythiophenol (I) with 4-methoxyphenacyl bromide (II) by means of KOH in ethanol gives 2-(4-methoxyphenyl)-6-methoxybenzothiophene (III),which is treated with pyridinium hydrochloride at 220 C to yield 2-(4-hydroxyphenyl)-6-hydroxybenzothiophene (IV).The protection of the hydroxy groups of (IV) by reaction with 4-chlorophenacyl bromide (V) and K2CO3 - 18-crown 6 in refluxing ether affords the bis p-chlorophenacyloxy derivative (VI),which by a Friedel-Kraft's reaction with 4-(2-pyrrolidinoethoxy)benzoyl chloride (VII) by means of AlCl3 in refluxing dichloroethane is converted into 2-[4-(4-chlorophenacyloxy)phenyl]-3-[4-(2-pyrrolidinoethoxy)benzoyl]-6-(4-chlorophenacyloxy)benzothiophene (VIII).Finally,this compound is deprotected by treatment with Zn and acetic acid.
参考文献标题:2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents
文献作者:Jones,C.D.; Suarez,T.
参考来源:DE 2647907; ES 452694; ES 452695; FR 2329271; GB 1570610; JP 52053851; US 4133814
合成路线:The cyclization of 3-methoxythiophenol (I) with 4-methoxyphenacyl bromide (II) by means of KOH in ethanol gives 2-(4-methoxyphenyl)-6-methoxybenzothiophene (III),which is treated with pyridinium hydrochloride at 220 C to yield 2-(4-hydroxyphenyl)-6-hydroxybenzothiophene (IV).The protection of the hydroxy groups of (IV) by reaction with 4-chlorophenacyl bromide (V) and K2CO3 - 18-crown 6 in refluxing ether affords the bis p-chlorophenacyloxy derivative (VI),which by a Friedel-Kraft's reaction with 4-(2-pyrrolidinoethoxy)benzoyl chloride (VII) by means of AlCl3 in refluxing dichloroethane is converted into 2-[4-(4-chlorophenacyloxy)phenyl]-3-[4-(2-pyrrolidinoethoxy)benzoyl]-6-(4-chlorophenacyloxy)benzothiophene (VIII).Finally,this compound is deprotected by treatment with Zn and acetic acid.
参考文献标题:LY-117018
文献作者:Blancafort,P.; Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1982,7(2),112
产品链接: CAS No. 63676-25-5››