dl-萘普生重排合成的工艺研究Ⅲ |
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引用本文: | 陈芬儿,沈怡,李艳,万江陵,张海云.dl-萘普生重排合成的工艺研究Ⅲ[J].中国医药工业杂志,1994(5). |
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作者姓名: | 陈芬儿 沈怡 李艳 万江陵 张海云 |
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作者单位: | 武汉化工学院制药研究室,青岛制药厂,海南省药检所 |
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摘 要: | 在三甲基氯硅烷的存在下,丙酰萘甲醚、乙二醇和原位形成的溴合二烷—锅反应转化成2-(1-溴乙基)-2-(6-甲氧基-2-萘基)-1,3-二氧戊环(3),再经重排、水解即得dl-萘普生。对丙酰萘甲醚计算,总收率91.5%。探讨了反应温度和不同溶剂对3收率的影响。还考察添加不同Lewis酸对氧化锌催化3重排时间的影响。
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关 键 词: | dl-萘普生,溴合二 烷,一锅合成,重排,合成 |
SYNTHESIS OF dl-NAPROXEN BY 1,2-ARYL REARRANGEMENT III |
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Authors: | CHEN Fen-Er SHEN Yi LI Yan WANG Jiang-Ling ZHANG Hai-Yun |
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Abstract: | Propinony1-6-methoxynaphthalen (2) was converted to 2-(1-bromoethyl)-2-(6-methoxy-2-naphthyl)-1, 3-dioxolane (3) by reaction with ethylene glycol and dioxane dibromide generated in situ in the presence of chlorotrimethylsilane. The rearrangement of 3 followed by hydrolysis afforded dl-naproxen in an overall yield of about 91.5%. The effect of reaction temperature and different solvents on yield was investigated.The influene on the time of rearrangement catalyzed by ZnO with addition of different Lewis acids was also observed. |
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Keywords: | dl-naproxen dioxane dibromide one-pot synthesis rearrangement synthesis |
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