HRID1198959

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1

HCID17453

Methyl (triphenylphosphoranylidene)acetate

C21H19O2P

HCID31275

1,4-Dioxane

C4H8O2

结构：COc1cc(C(=O)OC(C)(C)C)ccc1Cn1cc(C=O)c2ccc(C(=O)NCC3CCCC3)cc21

HCID15013776

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C=Cc1cn(Cc2ccc(C(=O)OC(C)(C)C)cc2OC)c2cc(C(=O)NCC3CCCC3)ccc12

HCID54500983

未命名化合物

收率 84%

PROCEDURE

实验过程

A solution of t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-formylindol-1-ylmethyl]-3-methoxybenzoate (1.2 g) and methyl (triphenylphosphoranylidene)acetate (1.8 g) in dioxane (12 ml) was heated at reflux for 48 hours. The solvent was evaporated. The resultant residue was purified by flash chromatography on silica gel (600 ml), eluting with 3:7 ethyl acetate:hexane, to give t-butyl 4-[6-(N-cyclopentylmethylcarbamoyl)-3-(2-methoxycarbonylvinyl)indol-1-ylmethyl]-3-methoxybenzoate (1.1 g, 84%) as a yellow solid; mp 163°-164°.

WORKUP

后处理

temperatureat reflux for 48 hours
customThe solvent was evaporated
customThe resultant residue was purified by flash chromatography on silica gel (600 ml)
washeluting with 3:7 ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4a9070751ca749af8a796669187dc9c4
来源数据集: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04898863
来源说明: uspto-grants-1990_02

反应 SMILES

[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14](C=O)=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(P(=[CH:56][C:57]([O:59][CH3:60])=[O:58])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOC[CH2:62]1>>[CH:1]1([CH2:6][NH:7][C:8]([C:10]2[CH:18]=[C:17]3[C:13]([C:14]([CH:62]=[CH:56][C:57]([O:59][CH3:60])=[O:58])=[CH:15][N:16]3[CH2:19][C:20]3[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:22][C:21]=3[O:33][CH3:34])=[CH:12][CH:11]=2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1