Tetrahydrofuran → HCID 58071501, compound

HRID 1471982Notes

Reaction equation

HRID 1471982 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 the desired compound (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-67e30a36409c41aba0d27bf1766b3bc1
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

Loading…