反応 #1951062

反応方程式

Cyclopropylmethyl-phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

(cyclopropylmethyl)-divinyl-phosphine oxide

収率 47.0%

反応条件

後処理

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   抽出The product was extracted into dichloromethane
4. 4
   洗浄washed with saturated aqueous sodium bicarbonate
5. 5
   乾燥The organic phase was dried with sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated by rotary evaporation

実験手順

Cyclopropylmethyl-phosphonic dichloride (8.43 g, 48.7 mmol) was dissolved in dry THF (70 mL), placed under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise vinyl magnesium bromide in THF (122 mL, 1 M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2 M) was chilled to 0° C. and stirred rapidly while the cold reaction mixture was added. The product was extracted into dichloromethane and washed with saturated aqueous sodium bicarbonate and then with water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 3.56 g of (cyclopropylmethyl)-divinyl-phosphine oxide (22.8 mmol, 47%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.44-6.14 (m, 6H); 1.84-1.78 (d of d, 2H) 0.98-0.86 (m, 1H); 0.66-0.60 (m, 2H); 0.25-0.19 (m, 2H); ESMS (m/z): (M+1)+ found, 157; (M−1)− found, 155.

出典