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【结 构 式】 
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【分子编号】40141 【品名】diethyl 3-oxopentanedioate 【CA登记号】105-50-0 |
【 分 子 式 】C9H14O5 【 分 子 量 】202.20716 【元素组成】C 53.46% H 6.98% O 39.56% |
合成路线1
该中间体在本合成路线中的序号：(X)The starting product ethyl 1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate (I) can be obtained by condensation of diethyl acetonedicarboxylate (X) with chloroacetone (IX) by means of methylamine in water, the compound (XI) being formed as an intermediate which is not isolated. The Friedel-Crafts aroylation of (I) with p-chlorobenzoyl chloride (B) and AlCl3 in refluxing dichloroethane gives ethyl 5-(p-chlorobenzoyl)-1,4-dimethyl-3-ethoxycarbonylpyrrole-2-acetate (VI), which by hydrolysis with aqueous 1N NaOH yields 5-(p-chlorobenzoyl)-1,4-dimethyl-3-carboxypyrrole-2-acetic acid (VII). The partial esterification of (VII) with ethanol and HCl produces ethyl 5-(p-chlorobenzoyl)-1,4-dimethyl-3-carboxypyrrole-2-acetate (VIII), which by decarboxylation at 210-30 C is converted into the ester (V) already obtained.
| 【1】 Carson, J.R.; Aroyl-substituted pyrroles. DE 2102746; FR 2081455; GB 1327308; JP 55033401; JP 55033402; US 3752826; US 3865840; US 4070368 . |
| 【2】 Hillier, K.; Castañer, J.; Zomepirac. Drugs Fut 1977, 2, 10, 698. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 10295 | p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride | 122-01-0 | C7H4Cl2O | 详情 | 详情 |
| (I) | 40135 | ethyl 2-(2-ethoxy-2-oxoethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylate | C13H19NO4 | 详情 | 详情 | |
| (V) | 40140 | ethyl 2-[5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetate | C17H18ClNO3 | 详情 | 详情 | |
| (VI) | 40143 | ethyl 5-(4-chlorobenzoyl)-2-(2-ethoxy-2-oxoethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylate | C20H22ClNO5 | 详情 | 详情 | |
| (VII) | 40144 | 2-(carboxymethyl)-5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-3-carboxylic acid | C16H14ClNO5 | 详情 | 详情 | |
| (VIII) | 40145 | 5-(4-chlorobenzoyl)-2-(2-ethoxy-2-oxoethyl)-1,4-dimethyl-1H-pyrrole-3-carboxylic acid | C18H18ClNO5 | 详情 | 详情 | |
| (IX) | 15288 | 1-Chloroacetone; Chloroacetone | 78-95-5 | C3H5ClO | 详情 | 详情 |
| (X) | 40141 | diethyl 3-oxopentanedioate | 105-50-0 | C9H14O5 | 详情 | 详情 |
| (XI) | 40142 | methanaminium 1-chloro-6-ethoxy-3-(ethoxycarbonyl)-2-methyl-4,6-dioxo-2-hexanolate | C13H24ClNO6 | 详情 | 详情 |