6-2-氨丙基-2,3-二氢苯并呋喃的合成工艺研究

Process for the Synthesis of 6-(2-Aminopropyl)-2,3-dihydrobenzofuran

摘要:

以3-甲氧基苯甲醛为原料，经亨利反应、还原硝基和双键、氨基保护、傅-克酰基化、脱甲基、环合、羰基还原等反应，合成目的产物6-2-氨丙基-2,3-二氢苯并呋喃。并对硝基和双键的还原反应、傅-克酰基化和脱甲基反应的工艺条件进行了优化，得出较佳工艺条件：(1) 还原反应：反应温度40 ℃，氢气压力4.0 MPa，Raney-Ni质量为化合物2的质量的8 %，产物收率为78.6 %；（2）合成化合物6的较佳工艺条件：反应温度45 ℃，n(氯乙酰氯)：n(化合物4)=1.4：1，反应时间为6 h，产物的收率为68.8 %。

Abstract:

6-(2-Aminopropyl)-2,3–dihydrobenzofuran was synthesized from 3-6-2-Aminopropyl-2,3–dihydrobenzofuran was synthesized from 3-methoxybenzaldeh -yde via a sequence of Henry Reaction, reduction of nitro group and double bond, amino -protection, Friedel-Crafts acetylation, demethylation, reduction of carbonyl group and cyclization. The reduction of nitro group and double bond, Friedel-Crafts acetylation and demethylation reactions were optimized to give the better reaction conditions. (1) Reduction: reaction temperature 40 ℃, reaction pressure 4.0 MPa, the amount of Raney-Ni to the compound 2 as 8 %, thus serving 78.6 % yield for the corresponding product, (2) Better process conditions for the synthesis of 6: Reaction temperature 40 ℃, n (chloroacetyl chloride)：n(product 4)=1.4:1, reaction time 6 h, thus serving 68.8 % yield for the product 6.