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

반응식

[CH:1]([P:4](Cl)(Cl)=[O:5])([CH3:3])[CH3:2].[CH:8]([Mg]Br)=[CH2:9].[NH4+].[Cl-].[CH2:14]1COC[CH2:15]1>>[CH:14]([P:4](=[O:5])([CH:8]=[CH2:9])[CH:1]([CH3:3])[CH3:2])=[CH2:15]

참가 물질

반응물 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 2793751Isopropylphosphonic dichloride

HCID 178418507HCID 178418507, 화합물

생성물 1

HCID 86658246Diethenyl(propan-2-yl)phosphane oxide수율 80%

반응 조건

온도: -78 °C

실험 절차

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.