【结 构 式】 |
【分子编号】55600 【品名】ethyl 4-[4-(methoxymethoxy)phenyl]butanoate 【CA登记号】 |
【 分 子 式 】C14H20O4 【 分 子 量 】252.3104 【元素组成】C 66.65% H 7.99% O 25.36% |
合成路线1
该中间体在本合成路线中的序号:(XII)The intermediate carboxylic acid (XIII) was prepared as follows: 2-(4-Hydroxyphenyl)ethanol (VI) was selectively protected at the phenolic hydroxyl with benzyl bromide, yielding (VII). Subsequent oxidation of the aliphatic alcohol group of (VII) with Dess-Martin periodinane reagent provided aldehyde (VIII). Wadsworth-Emmons condensation of (VIII) with the sodium derivative of phosphonate (IX) furnished adduct (X), which was further hydrogenated over Pd/C to the saturated ester (XI). The phenolic hydroxyl group of (XI), which was concomitantly debenzylated in the preceding hydrogenation step, was further reprotected as the methoxymethyl ether (XII). Acid (XIII) was then obtained by basic hydrolysis of ester (XII).
【1】 Takaoka, E.; et al.; Catalytic asymmetric synthesis of arbutamine. Heterocycles 1997, 46, 157. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 47355 | 4-(2-hydroxyethyl)phenol | 501-94-0 | C8H10O2 | 详情 | 详情 |
(VII) | 33328 | 2-(p-Benzyloxyphenyl)ethanol; 2-[4-(Benzyloxy)phenyl]-1-ethanol | C15H16O2 | 详情 | 详情 | |
(VIII) | 55597 | 2-[4-(benzyloxy)phenyl]acetaldehyde | C15H14O2 | 详情 | 详情 | |
(IX) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
(X) | 55598 | ethyl (E)-4-[4-(benzyloxy)phenyl]-2-butenoate | C19H20O3 | 详情 | 详情 | |
(XI) | 55599 | ethyl 4-(4-hydroxyphenyl)butanoate | C12H16O3 | 详情 | 详情 | |
(XII) | 55600 | ethyl 4-[4-(methoxymethoxy)phenyl]butanoate | C14H20O4 | 详情 | 详情 | |
(XIII) | 55601 | 4-[4-(methoxymethoxy)phenyl]butanoic acid | C12H16O4 | 详情 | 详情 |