Tetrahydrofuran → HCID 57925986, compound

HRID 1013455Notes

Reaction equation

HRID 1013455 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](Cl)(Cl)=[O:10])=[CH:5][CH:4]=1.[CH2:13]1[CH2:17]OCC1.[CH:18]([Mg]Br)=[CH2:19]>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:10])([CH:18]=[CH2:19])[CH:13]=[CH2:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 216711Phosphonic dichloride, (p-methoxyphenyl)-HCID 178418507HCID 178418507, compound

Product 1

HCID 57925986HCID 57925986, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(4-Methoxyphenyl)phosphonic dichloride (2.00 g, 8.89 mmol) was made 0.1 M in 1:1 THF:ether and stirred at −78° C. To this stirring solution vinyl magnesium bromide (17.8 mL, 17.78 mmol, 1M in THF) was added dropwise. The mixture was stirred for 1 h, then quenched with 2M aq. HCl and extracted with DCM (3×). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to afford the requisite product. MS: cal'd 209 (MH+), exp 209 (MH+)

Workup

  1. customquenched with 2M aq. HCl
  2. extractionextracted with DCM (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford the requisite product

Sources & evidence

ORD record
ord-1916c2b9b7744bfc891888a625c187c5
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…