Tetrahydrofuran → HCID 66833314, compound

Temperature

-70 °C

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, 1M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2M) 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.

1. stirringstirred rapidly while the cold reaction mixture
2. additionwas added
3. extractionThe product was extracted into dichloromethane
4. washwashed with saturated aqueous sodium bicarbonate
5. dry with materialThe organic phase was dried with sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation

ORD record

ord-ff8e1aa0506d4a2c83359d7510a0850e

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067395B2