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【结 构 式】

【分子编号】12844

【品名】(4-Iodophenyl)lithium

【CA登记号】

【 分 子 式 】C6H4ILi

【 分 子 量 】209.94323

【元素组成】C 34.33% H 1.92% I 60.45% Li 3.31%

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:(B)

Initially, a small-scale synthetic route to idoxifene had been described involving Friedel-Crafts acylation of 2-chloroethoxybenzene by 2-phenylbutyric acid followed by reaction of the resulting ketone with 4-iodophenyllithium (prepared by monolithiation of 1,4-diiodobenzene) . A mixture of E and Z isomers of the triphenylbutene was then produced by dehydration of the intermediate tertiary alcohol from which the desired E isomer (in which the unsubstituted phenyl and iodophenyl residues are in a trans relationship) was separated by crystallization. Idoxifene was then produced by final modification of the chloroethoxy side chain using pyrrolidine. Modification of the above scheme to provide an efficient, large-scale synthesis of idoxifene has now been described initially involving treatment of 2-phenoxyethanol with pyridine (in catalytic amounts) and thionyl chloride/heat to produce 2-chloroethoxybenzene.

1 Kelland, L.R.; Jarman, M.; Idoxifene. Drugs Fut 1995, 20, 7, 666.
2 Potter, G.A.; Jarman, M.; McCague, R.; An efficient, large-scale synthesis of idoxifene ((E)-1-[4-[N-(pyrrolidino)ethoxy]phenyl]-1-(4-iodophenyl)-2-phenyl-1-butene). Org Prep Proced Int 1994, 26, 343-6.
3 McCague, R. (National Research Development Corp.); Tamoxifen derivs. EP 0260066; GB 2196003; JP 1988077845 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 12844 (4-Iodophenyl)lithium C6H4ILi 详情 详情
(A) 21130 2-Phenylbutyric acid; alpha-Ethylbenzeneacetic acid 90-27-7 C10H12O2 详情 详情
(I) 12841 2-Phenoxyethanol; 2-Phenoxy-1-ethanol 122-99-6 C8H10O2 详情 详情
(II) 12842 2-Chloroethyl phenyl ether; b-Chlorophenetole; 1-(2-Chloroethoxy)benzene 622-86-6 C8H9ClO 详情 详情
(III) 12843 1-[4-(2-Chloroethoxy)phenyl]-2-phenyl-1-butanone C18H19ClO2 详情 详情
(IV) 12845 2-Chloroethyl 4-[(E)-1-(4-iodophenyl)-2-phenyl-1-butenyl]phenyl ether; 1-[(E)-1-[4-(2-Chloroethoxy)phenyl]-2-phenyl-1-butenyl]-4-iodobenzene C24H22ClIO 详情 详情
(V) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
Extended Information