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【结 构 式】 
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【分子编号】35849 【品名】1-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-2-propen-1-one 【CA登记号】 |
【 分 子 式 】C12H6F4O2 【 分 子 量 】258.1720528 【元素组成】C 55.83% H 2.34% F 29.44% O 12.39% |
合成路线1
该中间体在本合成路线中的序号：(III)The Grignard reaction of 7-fluoro-4-(trifluoromethyl)benzofuran-2-carbaldehyde (I) with vinylmagnesium bromide in ether/THF gives the expected carbinol (II), which is oxidized with MnO2 in dichloromethane yielding the propenone (III). The condensation of (III) with 4-formylbenzoic acid methyl ester (IV) by means of 3-benzyl-5-(hydroxymethyl)-4-methylthiazolium chloride (BHMT) in refluxing ethanol affords the 1,4-butanedione (V), which is cyclized with ammonium acetate in refluxing methanol to give the substituted pyrrole (VI). Finally, the ester group of (V) is hydrolyzed with NaOH in refluxing ethanol/water.
| 【1】 Tagami, K.; Yoshimura, H.; Nagai, M.; Hibi, S.; Kikuchi, K.; Sato, T.; Okita, M.; Okamoto, Y.; Nagasaka, Y.; Kobayashi, N.; Hida, T.; Tai, K.; Tokuhara, N.; Kobayashi, S. (Eisai Co., Ltd.); Fused-ring carboxylic acid derivs.. EP 0889032; US 6110959; US 6121309; WO 9734869 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16524 | bromo(vinyl)magnesium | 1826-67-1 | C2H3BrMg | 详情 | 详情 | |
| (I) | 35847 | 7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-carbaldehyde | C10H4F4O2 | 详情 | 详情 | |
| (II) | 35848 | 1-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-2-propen-1-ol | C12H8F4O2 | 详情 | 详情 | |
| (III) | 35849 | 1-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-2-propen-1-one | C12H6F4O2 | 详情 | 详情 | |
| (IV) | 10170 | methyl 4-formylbenzoate | 1571-08-0 | C9H8O3 | 详情 | 详情 |
| (V) | 35850 | methyl 4-[4-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-4-oxobutanoyl]benzoate | C21H14F4O5 | 详情 | 详情 | |
| (VI) | 35851 | methyl 4-[5-[7-fluoro-4-(trifluoromethyl)-1-benzofuran-2-yl]-1H-pyrrol-2-yl]benzoate | C21H13F4NO3 | 详情 | 详情 |