Tetrahydrofuran → HCID 58071501, compound

HRID 921365Notes

Reaction equation

HRID 921365 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:12](Cl)(Cl)=[O:13])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[CH:16]([Mg]Br)=[CH2:17].[CH2:20]1COC[CH2:21]1>>[CH:20]([P:12](=[O:13])([CH:16]=[CH2:17])[C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH2:21]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 58523430HCID 58523430, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 58071501HCID 58071501, compoundYield 75%

Conditions

Temperature
-78 °C

Procedure

To a solution of (3-methoxy-4-nitrophenyl)phosphonic dichloride (1.39 g, 5.15 mmol) in 15 mL THF at −78° C. under nitrogen was slowly added vinylmagnesium bromide (10.3 mL, 1.0 M in THF). After the addition was complete, the reaction stirred at −78° C. for an additional hour. The cold reaction mixture was quenched by the addition of saturated NH4Cl (20 mL) and the mixture was extracted with CH2Cl2. The combined organic layers were washed with 1 M NaOH, brine, and dried over MgSO4. The organic extracts were filtered and concentrated to provide Diethenyl(3-methoxy-4-nitrophenyl)phosphane oxide (0.982 g, 75%).

Workup

  1. customat −78° C.
  2. additionAfter the addition
  3. customThe cold reaction mixture
  4. customwas quenched by the addition of saturated NH4Cl (20 mL)
  5. extractionthe mixture was extracted with CH2Cl2
  6. washThe combined organic layers were washed with 1 M NaOH, brine
  7. dry with materialdried over MgSO4
  8. filtrationThe organic extracts were filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f03a442333de47319da589a3a7932fbb
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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