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【结 构 式】 
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【分子编号】69020 【品名】methyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate 【CA登记号】 |
【 分 子 式 】C13H18O3 【 分 子 量 】222.28412 【元素组成】C 70.24% H 8.16% O 21.59% |
合成路线1
该中间体在本合成路线中的序号：(XIXb)Coupling of 2-(4-bromophenyl)ethanol (XVII) with dimethylketene ethyl trimethylsilyl acetal (XVIIIa) in the presence of Pd(dba)2, (t-Bu)3P and ZnF2 in DMF at 80 °C gives the 2-arylisobutyrate ester (XIXa). Subsequent hydroxyl group sulfonylation in (XIXa) with MsCl and Et3N in CH2Cl2 yields the mesylate ester (XIV).
Similarly, 2-(4-bromophenyl)ethanol (XVII) (optionally pretreated with HMDS and NH4Cl in MeCN) is coupled with dimethylketene methyl trimethylsilyl acetal (XVIIIb) in the presence of Pd(dba)2, (t-Bu)3P and ZnF2 in DMF at 80 °C, giving 2-arylisobutyrate ester (XIXb), which is then sulfonylated with MsCl in the presence of Et3N in CH2Cl2, affording synthon (XV) .
| 【1】 Lee, C.-H., Khoo, J.-H., Kwon, K.-C., Ju, H. (Yuhan Corp.). Process for preparation of 2-methyl-2’-phenylpropionic acid derivatives and novel intermediate compounds. WO 2009102155. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVIIIa) | 44478 | 1-Ethoxy-2-methyl-1-trimethylsiloxypropene;1-Ethoxy-2-methyl-1-(trimethylsilyloxy)propene;1-Ethoxy-2-methyl-1-(trimethylsilyl)oxy-1-propene;1-ethoxy-2-methyl-1-propenyl trimethylsilyl ether; [(1-ethoxy-2-methyl-1-propenyl)oxy](trimethyl)silane ;dimethylketene ethyl trimethylsilyl acetal | 31469-16-6 | C9H20O2Si | 详情 | 详情 |
| (XVIIIb) | 42016 | 1-Methoxy-2-methyl-1-(trimethylsiloxy)propene;1-Methoxy-2,2-dimethyl-1-(trimethylsiloxy)ethene;1-Methoxy-1-(trimethylsilyloxy)-2-methylpropene;[(1-methoxy-2-methyl-1-propenyl)oxy](trimethyl)silane; 1-methoxy-2-methyl-1-propenyl trimethylsilyl ether ;dimethylketene methyl trimethylsilyl acetal | 31469-15-5 | C8H18O2Si | 详情 | 详情 |
| (XIXa) | 69019 | ethyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate | C14H20O3 | 详情 | 详情 | |
| (XIXb) | 69020 | methyl 2-(4-(2-hydroxyethyl)phenyl)-2-methylpropanoate | C13H18O3 | 详情 | 详情 | |
| (XIV) | 69016 | ethyl 2-methyl-2-(4-(2-((methylsulfonyl)oxy)ethyl)phenyl)propanoate | C15H22O5S | 详情 | 详情 | |
| (XV) | 69018 | methyl 2-methyl-2-(4-(2-((methylsulfonyl)oxy)ethyl)phenyl)propanoate | C14H20O5S | 详情 | 详情 | |
| (XVII) | 14248 | 2-(4-Bromophenyl)-1-ethanol; 4-Bromophenethyl alcohol；2-(4-bromophenyl)ethanol；2-(4-Bromophenyl)ethan-1-ol | 4654-39-1 | C8H9BrO | 详情 | 详情 |