反応 #349396

反応方程式

product

2-bromo-7-(2-hydroxyethyl)-3-phenylbenzofuran

acetic acid

acetic acid

dinitrogen tetraoxide

4-cyclohexenecarboxylic acid

→

2-(2-nitro-3-phenyl-7-benzofuranyl)ethyl acetate

溶媒

hexane chloroform

hexane chloroform

反応条件

後処理

1. 1
   温度the mixture is heated at 45° C. for one hour
2. 2
   workup.WAITat 55° C. for one hour
3. 3
   その他The mixture is then partially evaporated
4. 4
   その他to remove residual dinitrogen tetraoxide
5. 5
   workup.ADDITIONpoured into water
6. 6
   抽出extracted with diethyl ether
7. 7
   洗浄The ether extracts are washed thrice with water
8. 8
   乾燥twice with sodium bicarbonate solution, once with water, and dried
9. 9
   その他Evaporation
10. 10
    その他provides a residue which
11. 11
    その他are obtained
12. 12
    その他Recrystallization of the first main component twice from a hexanebenzene mixture

実験手順

The product of step A and 2 g. of 4-cyclohexenecarboxylic acid are dissolved in 25 ml. of acetic acid, and 1.8 g. of dinitrogen tetraoxide in 5 ml. of acetic acid are added dropwise. After stirring 20 minutes at room temperature, the mixture is heated at 45° C. for one hour, then at 55° C. for one hour. The mixture is then partially evaporated to remove residual dinitrogen tetraoxide, poured into water, then extracted with diethyl ether. The ether extracts are washed thrice with water, twice with sodium bicarbonate solution, once with water, and dried. Evaporation provides a residue which is dissolved in hexane-chloroform and fractionated by chromatography on silica gel, using hexane-chloroform as eluent. Thin layer chromatographic analysis determines that two relatively pure components are obtained. Recrystallization of the first main component twice from a hexanebenzene mixture provides yellow flakes of 2-(2-nitro-3-phenyl-7-benzofuranyl)ethyl acetate, m.p. 95°-98° C.

出典