反応 #1951060

反応方程式

Bromomethyl-cyclopropane

triisopropyl phosphite

→

cyclopropylmethyl-phosphonic acid diisopropyl ester

収率 94.3%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to cool to ambient temperature
3. 3
   洗浄The solution was washed with saturated sodium bicarbonate (350 mL)
4. 4
   乾燥The organic phase was dried with magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated by rotary evaporation

実験手順

Bromomethyl-cyclopropane (26.00 g, 0.193 mol) was added to triisopropyl phosphite (35.9 mL, 0.30 mol) at ambient temperature, under a nitrogen atmosphere. The resulting solution was stirred and heated at reflux (144° C. bath temperature) overnight. The reaction mixture was allowed to cool to ambient temperature and then ethyl acetate (350 mL) was added. The solution was washed with saturated sodium bicarbonate (350 mL) and then with saturated brine (2×350 mL). The organic phase was dried with magnesium sulfate, filtered, and concentrated by rotary evaporation and then under high vacuum to yield 39.96 g of cyclopropylmethyl-phosphonic acid diisopropyl ester (0.182 mol, 94% yield) as a colorless oil. 1H NMR (400 MHz, DMSO) δ 4.63-4.54 (m, 2H); 1.67-1.60 (d of d, 2H) 1.27-1.24 (d of d, 12H); 0.85-0.75 (m, 1H); 0.52-0.46 (m, 2H); 0.21-0.16 (m, 2H); ESMS (m/z): M+1)+ found, 221; (M+23)+ found, 243.

出典