HRID652540

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7449

3-Nitrobenzaldehyde

C7H5NO3

HCID643918

2-Butenoic acid, 3-amino-, methyl ester, (2Z)-

C5H9NO2

结构：CC1(C)OCC(COC(CCc2ccccc2)C(=O)CC(=O)[O-])O1

HCID131715180

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C1=C(C)NC(C)=C(C(=O)OCCc2ccc(OCC3COC(C)(C)O3)cc2)C1c1cccc([N+](=O)[O-])c1

HCID13632564

未命名化合物

收率 95%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID702

Ethanol

C2H6O

PROCEDURE

实验过程

A solution of 13.2 g. (0.039 mol) of 4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenylethylacetoacetate (5), 4.7 g (0.41 mol) of methyl β-aminocrotonate, and 6.2 g (0.41 mol) of 3-nitrobenzaldehyde in 80 mL of ethanol was heated at reflux for 12 h. Solvent was removed in vacuo and the residue purified by medium pressure chromatography on silica gel (80% ether-hexane) to give 21 g of 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxyphenyl]ethoxycarbonyl)-1,4-dihydropyridine (6) as an orange oil.

WORKUP

后处理

temperatureat reflux for 12 h
customSolvent was removed in vacuo
customthe residue purified by medium pressure chromatography on silica gel (80% ether-hexane)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-510265164e6f43a8adc99ce73ad53a5d
来源数据集: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US04672071
来源说明: uspto-grants-1987_06

反应 SMILES

[CH3:1][C:2]1([CH3:24])[O:6][CH:5]([CH2:7][O:8][CH:9]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22]C=[CH:20][CH:19]=2)C(=O)CC([O-])=O)[CH2:4][O:3]1.[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29].[N+:33]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH:39]=O)([O-:35])=[O:34]>C(O)C>[CH3:32][C:26]1[NH:25][C:26]([CH3:32])=[C:27]([C:28]([O:30][CH2:22][CH2:23][C:18]2[CH:17]=[CH:16][C:9]([O:8][CH2:7][CH:5]3[CH2:4][O:3][C:2]([CH3:1])([CH3:24])[O:6]3)=[CH:20][CH:19]=2)=[O:29])[CH:39]([C:38]2[CH:41]=[CH:42][CH:43]=[C:36]([N+:33]([O-:35])=[O:34])[CH:37]=2)[C:27]=1[C:28]([O:30][CH3:31])=[O:29]