Acetic Acid → 2-(3,4-Dichlorophenyl)-5-(2-nitrovinyl)furan

温度

0 °C

A stirred solution of acetic acid (1.4 ml, 1.46 g, 24.3 mmol) in methanol (3.5 ml) under nitrogen atmosphere at 0° C. was treated dropwise with n-propylamine (2.0 ml, 1.42 g, 24.0 mmol). The resulting n-propylammonium acetate solution was stirred at 0° C. for 5 min, then added dropwise to a stirred solution of 5-(3,4-dichlorophenyl)furfural (10.04 g, 41.6 mmol) in nitromethane (6.8 ml, 7.61 g, 124.7 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 30 min. Then the cooling bath was removed, and stirring was continued at RT. From time to time, 10 ml of THF was added five times. After stirring overnight THF was evaporated and water was added. A solid was filtrated, washed with water and heptane to afford 11.46 g of 2-(3,4-dichlorophenyl)-5-((E)-2-nitrovinyl)furan. 1H NMR (400 MHz, DMSO-d6): 7.38 (1H, d), 7.43 (1H, d), 7.76 (1H, d), 7.95 (1H, dd), 8.03 (1H, d), 8.19 (1H, d), 8.31 (1H, d)

1. customThen the cooling bath was removed
2. stirringstirring
3. customwas continued at RT
4. additionFrom time to time, 10 ml of THF was added five times
5. stirringAfter stirring overnight THF
6. customwas evaporated
7. additionwater was added
8. filtrationA solid was filtrated
9. washwashed with water and heptane

ORDレコード

ord-02b842f831f0463fb14cebfedd74b007

出典データセット

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08975254B2