Tetrahydrofuran → Diethenyl(propan-2-yl)phosphane oxide

Participants

Reaction Conditions

Reaction Steps

A 20 L four-necked round bottom flask fitted with an overhead stirrer and dropping funnel, flame dried and cooled in a stream of nitrogen, was charged with isopropyl phosphonic dichloride (350.0 g, 2173 mmol) in THF (5000 mL). The mixture was cool to −78° C. and vinyl magnesium bromide (5217 mL, 5217 mmol, 1M in THF) was added dropwise over 4 h. The reaction mixture was stirred at −78° C. for additional 30 minutes. After completion, the reaction mixture was poured into cold saturated aqueous NH4Cl (3.5 L) and extracted with dichloromethane (4×1000 L). The organic layers were combined, washed with brine (2×15000 mL), dried over sodium sulfate and concentrated in vacuo to give diethenyl(propan-2-yl)phosphane oxide (250 g, 80%) as light-brown oil.

Provenance & Evidence