L-651896
Chemical Name: 5-Hydroxy-6-[2-(hydroxymethyl)cinnamyl]-2,3-dihydrobenzofuran
CAS No. 99134-29-9, 120694-96-4 (E-isomer)
项目整合开发状态: Phase II
项目研究机构: Merck & Co. (Originator)
合成路线:The reduction of ethyl 2-bromocinnamate (I) with diisobutylaluminum hydride in toluene gives 2-bromocinnamyl alcohol (II),which is treated with PBr3 in CCl4 to afford 2-bromocinnamyl bromide (III).The condensation of (III) with 5-hydroxy-2,3-dihydrobenzofuran (IV) by means of NaH in hot benzene affords 6-(2-bromocinnamyl)-5-hydroxy-2,3-dihydrobenzofuran (V),which is treated with Cu2(CN)2 in N-methylpyrrolidone at 175 C to yield 6-(2-cyanocinnamyl)-5-hydroxy-2,3 dihydrobenzofuran (VI).Finally,this compound is reduced with diisobutylaluminum hydride in benzene,and treated with NaBH4 in methanol.
📌 参考资料/链接：
参考文献标题:Substd.cinnamyl-2,3-dihydrobenzopyrans and cinnamylphenols useful as anti-inflammatory agents
文献作者:Chang,M.N.; Hammond,M.I.; Jensen,N.P.; McDonald,J.; Zambias,R.A.(Merck & Co.,Inc.)
参考来源:EP 0143952; ES 8601951; JP 1985097924; US 4537903
📄 详细内容
合成路线:The reduction of ethyl 2-bromocinnamate (I) with diisobutylaluminum hydride in toluene gives 2-bromocinnamyl alcohol (II),which is treated with PBr3 in CCl4 to afford 2-bromocinnamyl bromide (III).The condensation of (III) with 5-hydroxy-2,3-dihydrobenzofuran (IV) by means of NaH in hot benzene affords 6-(2-bromocinnamyl)-5-hydroxy-2,3-dihydrobenzofuran (V),which is treated with Cu2(CN)2 in N-methylpyrrolidone at 175 C to yield 6-(2-cyanocinnamyl)-5-hydroxy-2,3 dihydrobenzofuran (VI).Finally,this compound is reduced with diisobutylaluminum hydride in benzene,and treated with NaBH4 in methanol.
参考文献标题:L-651896
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(11),939
产品链接: CAS No. 99134-29-9››