2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-[[(3,4-Dimethoxyphenyl)amino]methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:12](OCC)(OCC)OCC.[CH3:22][C:23]1([CH3:31])[O:28][C:27](=[O:29])[CH2:26][C:25](=[O:30])[O:24]1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][CH:12]=[C:26]2[C:27](=[O:29])[O:28][C:23]([CH3:31])([CH3:22])[O:24][C:25]2=[O:30])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

Edukt 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

HCID 227703,4-Dimethoxyaniline

HCID 31214Ethyl orthoformate

Produkt 1

HCID 212340935-[[(3,4-Dimethoxyphenyl)amino]methylene]-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 85,6 %

Versuchsvorschrift

A mixture of 3,4-dimethoxybenzenamine (10 g, 65 mmol) and CH(OC2H5)3 (96.2 g, 650 mmol) in a 500 mL of round-bottom flask was stirred at room temperature for 30 minutes. 2,2-Dimethyl-1,3-dioxane-4,6-dione (9.4 g, 65 mmol) was then added and the reaction mixture was heated at 90° C. for 3.5 h. The reaction solution was cooled at −20° C. overnight. The solid was collected by filtration and washed with 2-methoxy-2-methyl propane (50 mL×3) to afford the title compound as a pale yellow powder (17.1 g, 85.5%).