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【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information