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【结 构 式】

【分子编号】31187

【品名】methyl (E)-3-methoxy-2-butenoate

【CA登记号】

【 分 子 式 】C6H10O3

【 分 子 量 】130.1436

【元素组成】C 55.37% H 7.74% O 36.88%

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:(II)

Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords, after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III). Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV), which in acidic medium spontaneously lactonizes to give the parent compound.

1 Chatterjee, S.S.; Klessing, K. (Willmar Schwabe GmbH); 5-Arylalkyl-4-alkoxy-2(5H)-furanone derivs., intermediates and process for their preparation as well as use as therapeutic agents. DE 3615157; EP 0247320; JP 1988022087; US 4855320 .
2 Noldner, M.; Chatterjee, S.S.; LOSIGAMONE < Prop INN >. Drugs Fut 1990, 15, 10, 995.
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) 24114 2-chlorobenzaldehyde 89-98-5 C7H5ClO 详情 详情
(II) 31187 methyl (E)-3-methoxy-2-butenoate C6H10O3 详情 详情
(III) 31188 ethyl (2E,4E)-5-(2-chlorophenyl)-3-methoxy-2,4-pentadienoate C14H15ClO3 详情 详情
(IV) 31189 ethyl (E)-5-(2-chlorophenyl)-4,5-dihydroxy-3-methoxy-2-pentenoate C14H17ClO5 详情 详情
Extended Information