反应 #1951065

反应方程式

phosphorochloridic acid diethyl ester

cyclopropylmagnesium bromide

NH4Cl

→

cyclopropylphosphonic acid diethyl ester

收率 51.0%

溶剂

THF

反应条件

后处理

1. 1
   其他To a 200 mL round-bottom flask equipped with a magnetic stir-bar
2. 2
   温度to slowly warm to room temperature overnight
3. 3
   其他partitioned
4. 4
   萃取The product was extracted from the aqueous layer with diethyl ether (1×100 mL)
5. 5
   干燥dried over sodium sulfate
6. 6
   浓缩concentrated in vacuo
7. 7
   workup.DISTILLATIONThe resulting yellow oil was further purified by vacuum distillation (65-75° C. at 500 mTorr)

实验过程

To a 200 mL round-bottom flask equipped with a magnetic stir-bar was added phosphorochloridic acid diethyl ester (17.25 mL, 120 mmole) and THF (200 mL). The mixture was cooled to −78° C. and a solution of cyclopropylmagnesium bromide (200 mL, 0.5 M in THF, 100 mmol) was added dropwise over 30 minutes using an addition funnel. The reaction was allowed to slowly warm to room temperature overnight. The resulting clear reaction mixture was poured into saturated NH4Cl (200 mL) and partitioned. The product was extracted from the aqueous layer with diethyl ether (1×100 mL). The organic fractions were combined, dried over sodium sulfate, and concentrated in vacuo. The resulting yellow oil was further purified by vacuum distillation (65-75° C. at 500 mTorr) to provide cyclopropylphosphonic acid diethyl ester (9.025 g, 51%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 4.11-4.03 (m, 4H), 1.32-1.29 (m, 6H), 0.90-0.77 (m, 5H); 13C NMR (100 MHz, CDCl3) δ ppm 61.7 (d, J=5.3 Hz), 16.4 (d, J=6.1 Hz), 3.3 (d, J=196.3 Hz), 3.0 (d, J=4.6 Hz).

来源