Hydrochloric Acid → Diethenylphenylphosphine oxide

HRID 1013498Notes

Reaction equation

HRID 1013498 reaction equation
[C:1]1([P:7](Cl)(Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]1[CH2:15]OCC1.[CH:16]([Mg]Br)=[CH2:17].Cl>CCOCC>[C:1]1([P:7](=[O:8])([CH:16]=[CH2:17])[CH:11]=[CH2:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 69990Phenylphosphonic dichlorideHCID 178418507HCID 178418507, compound

Product 1

HCID 14223331Diethenylphenylphosphine oxide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

Phenylphosphonic dichloride (2.00 g, 10.26 mmol) was taken up in 1:1 THF:Et2O (100 mL) and cooled to −78° C. Vinylmagnesium bromide (21.54 mL, 21.54 mmol, 1.0 M in THF) was added dropwise. After stirring for 2 h at −78° C., the cold reaction was poured into 2 N HCl, and the mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to a yellow oil. Flash chromatography (0-10% MeOH/EtOAc) afforded phenyl(divinyl)phosphine oxide as a colorless solid. 1H NMR (CDCl3, 600 MHz) δ 7.72-7.67 (m, 2H), 7.54-7.50 (m, 1H), 7.49-7.45 (m, 2H), 6.44 (ddd, J=24.5, 18.7, 12.4 Hz, 2H), 6.29-6.18 (m, 4H). MS: cal'd 179 (MH+), exp 179 (MH+).

Workup

  1. customthe cold reaction
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to a yellow oil

Sources & evidence

ORD record
ord-bd255a62ec8f42a382c9035f2c8db3cf
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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