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【结 构 式】 
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【分子编号】50363 【品名】2-(2,2-dimethoxyethoxy)-3,6-dimethylbenzaldehyde 【CA登记号】 |
【 分 子 式 】C13H18O4 【 分 子 量 】238.28352 【元素组成】C 65.53% H 7.61% O 26.86% |
合成路线1
该中间体在本合成路线中的序号：(III)The condensation of 2-hydroxy-3,6-dimethylbenzaldehyde (I) with 2-bromoacetaldehyde dimethyl acetal (II) by means of K2CO3 in DM gives the phenoxyacetaldehyde acetal (III), which is cyclized by means of acetic acid to yield 4,7-dimethylbenzofuran (IV). The condensation of (IV) with 4-acryloylbenzoic acid methyl ester (V) by means of 3-benzyl-5-(hydroxymethyl)-4-methylthiazolium chloride (BHMT) and TEA in DMF affords the butanedione derivative (VI), which is cyclized to the pyrrole derivative (VII) by means of NH4OAc in refluxing methanol. Finally, the methyl ester group of (VII) is hydrolyzed with NaOH in ethanol to afford the target carboxylic acid.
| 【1】 Yoshimura, H.; et al.; Discovery of novel and potent retinoic acid receptor alpha agonists: Syntheses and evaluation of benzofuranyl-pyrrole and benzothiophenyl-pyrrole derivatives. J Med Chem 2000, 43, 15, 2929. |
| 【2】 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 |
|---|---|---|---|---|---|---|
| (I) | 50362 | 2-hydroxy-3,6-dimethylbenzaldehyde | C9H10O2 | 详情 | 详情 | |
| (II) | 13183 | 2-Bromo-1,1-dimethoxyethane; 2-Bromo-1-methoxyethyl methyl ether; Bromoacetaldehyde dimethyl acetal | 7252-83-7 | C4H9BrO2 | 详情 | 详情 |
| (III) | 50363 | 2-(2,2-dimethoxyethoxy)-3,6-dimethylbenzaldehyde | C13H18O4 | 详情 | 详情 | |
| (IV) | 35861 | 4,7-dimethyl-1-benzofuran-2-carbaldehyde | C11H10O2 | 详情 | 详情 | |
| (V) | 35857 | methyl 4-acryloylbenzoate | C11H10O3 | 详情 | 详情 | |
| (VI) | 35862 | methyl 4-[4-(4,7-dimethyl-1-benzofuran-2-yl)-4-oxobutanoyl]benzoate | C22H20O5 | 详情 | 详情 | |
| (VII) | 35863 | methyl 4-[5-(4,7-dimethyl-1-benzofuran-2-yl)-1H-pyrrol-2-yl]benzoate | C22H19NO3 | 详情 | 详情 |