Tetrahydrofuran → Diethenylphenylphosphine oxide

반응식

[C:1]1([P:7](Cl)(Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]([Mg]Br)=[CH2:12].[NH4+].[Cl-].[CH2:17]1COC[CH2:18]1>>[CH:17]([P:7](=[O:8])([CH:11]=[CH2:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:18]

참가 물질

반응물 4

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 69990Phenylphosphonic dichloride

HCID 178418507HCID 178418507, 화합물

생성물 1

HCID 14223331Diethenylphenylphosphine oxide수율 75%

반응 조건

온도: -78 °C

실험 절차

A solution of phenylphosphonic dichloride (29 mL, 200 mmol) dissolved in anhydrous THF (600 mL) was cooled to −78° C. and mechanically stirred under an atmosphere of dry nitrogen. Vinylmagnesium bromide (1M in THF, 500 mL) was slowly added so that the temperature of the reaction mixture never exceeded −70° C. The addition took 2 hours. After an additional 1 hour of stirring at −78° C., the cold reaction mixture was poured directly into cold, saturated NH4Cl (1 L). The mixture was extracted twice with CH2Cl2 and the combined organic phase was washed with 1 M NaOH, brine, and then dried over Mg2SO4. Filtration and solvent evaporation provided divinyl-phenyl-phosphine oxide (26.8 g, 75%) as a viscous yellow oil that solidified upon standing. 1H NMR (400 MHz, DMSO-d6); δ 7.8-7.4 (m, 5H), 6.7 (m, 2H), 6.4-6.1 (m, 4H). 31P NMR (DMSO-d6); δ 17.0 (s).