Réaction #1951062

Équation de réaction

Cyclopropylmethyl-phosphonic dichloride

THF

vinyl magnesium bromide

THF

ammonium chloride

→

(cyclopropylmethyl)-divinyl-phosphine oxide

Rendement 47.0%

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred rapidly while the cold reaction mixture
2. 2
   workup.ADDITIONwas added
3. 3
   ExtractionThe product was extracted into dichloromethane
4. 4
   Lavagewashed with saturated aqueous sodium bicarbonate
5. 5
   SéchageThe organic phase was dried with sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated by rotary evaporation

Mode opératoire

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.

Source