反応 #607922

反応方程式

NaNO2

cyclopropane

2,2-diphenylcyclopropanyl carboxylate ethyl ester

H2SO4

→

solid

収率 97.0%

5,5-diphenylisoxazoline carboxylate ethyl ester

収率 97.0%

溶媒

AcOH

—

petrol

water

反応条件

後処理

1. 1
   その他did not excess 40° C
2. 2
   workup.ADDITIONAfter addition
3. 3
   抽出extracted with diethyl ether (2×20 mL)
4. 4
   洗浄washed with sat. NaHCO3 (2×20 mL)
5. 5
   乾燥The washed ethereal solution was then dried over Na2SO4
6. 6
   その他After removing the desiccant
7. 7
   濃縮the ethereal solution was concentrated
8. 8
   その他to furnish a thick oily product

実験手順

The cyclopropane derivative, 2,2-diphenylcyclopropanyl carboxylate ethyl ester (1.0 g, 3.8 mmol) was dissolved in 4.0 mL AcOH at room temperature (18° C.). Into the solution was carefully added 2.0 mL concentrated H2SO4, followed by adding NaNO2 (0.29 g, 4.1 mmol, 1.1 eq) in several portions so that the reaction temperature did not excess 40° C. After addition, the reactants were stirred at room temperature (about 18° C.) for half an hour before the reactants were poured into iced water and extracted with diethyl ether (2×20 mL), the ethereal solutions were combined and washed with sat. NaHCO3 (2×20 mL), then water (20 mL) and brine (20 mL). The washed ethereal solution was then dried over Na2SO4. After removing the desiccant, the ethereal solution was concentrated to furnish a thick oily product. The 1H NMR of the crude product showed that the reaction was clean and the yield was virtually 100%. The thick oily crude product was stirred with 10 mL petrol to give a pale yellow solid 1.07 g, 97% yield.

出典