Tetrahydrofuran → HCID 57973306, compound

Temperature

-78 °C

To a 250 mL round-bottom flask equipped with a magnetic stir-bar was added cyclopropyl phosphonic dichloride (2.33 g, 14.7 mmol) and THF (100 mL). The solution was cooled to −78° C. and vinylmagnesium bromide (58.8 mmol, 1.0 M solution in THF) was added dropwise over 15 minutes. The solution was stirred at −78° C. for 7 hours and then poured, while still cold, into saturated aqueous NH4Cl (200 mL). The resulting solution was extracted with DCM (3×100 mL). The organic layers were combined, washed with brine (2×100 mL), dried over sodium sulfate and concentrated in vacuo to provide cyclopropyl-divinyl-phosphine oxide (0.811 g, 39%) as a light-brown free-flowing oil which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 6.40-6.00 (m, 6H), 0.98-0.80 (m, 5H); GC-CIMS (m/z): (M+1)+ found, 142.

1. customTo a 250 mL round-bottom flask equipped with a magnetic stir-bar
2. additionpoured
3. extractionThe resulting solution was extracted with DCM (3×100 mL)
4. washwashed with brine (2×100 mL)
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-8fc686f44ee94aafa0c3cc30d7430a40

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625880B2