Tetrahydrofuran → 1,3-Bis(diethylphosphonooxy)-4-ethylbenzene

HRID 449790Notes

Reaction equation

HRID 449790 reaction equation
[O:1]1[CH2:5][CH2:4]CC1.[CH2:6]([C:8]1[CH:14]=[CH:13][C:11]([OH:12])=[CH:10][C:9]=1[OH:15])[CH3:7].[H-].[Na+].[P:18](Cl)([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19]>O>[CH2:21]([O:20][P:18]([O:12][C:11]1[CH:13]=[CH:14][C:8]([CH2:6][CH3:7])=[C:9]([O:15][P:18]([O:1][CH2:5][CH3:4])([O:20][CH2:21][CH3:22])=[O:19])[CH:10]=1)([O:23][CH2:24][CH3:25])=[O:19])[CH3:22]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 179274-EthylresorcinolHCID 24758Sodium hydride

Product 1

HCID 545972611,3-Bis(diethylphosphonooxy)-4-ethylbenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a tetrahydrofuran solution (10 ml) of 4-ethylresorcinol (691 mg), sodium hydride (60% dispersion in liquid paraffin) (440 mg) was added and stirred at 0° C. for 30 minutes. Then, diethyl chlorophosphate (1.73 ml) was added dropwise. After stirring at room temperature for 3 hours, water (10 ml) was added to the reaction mixture, and the extraction was carried out with ethyl acetate (30 ml). Then, the extract was washed with saturated brine (10 ml), dried with anhydrous sodium sulfate and then concentrated. The residue (2.43 g) was subjected to silica gel chromatography (silica gel 40 g, chloroform to chloroform:methanol=10:1), to give the title compound (2.05 g, yield: 100%) as a pale yellow oil.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. extractionthe extraction
  3. washThen, the extract was washed with saturated brine (10 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-42cc9b0905be40cca21db77815f602f9
Source dataset
uspto-grants-2013_07
Patent number
US08486919B2

Reaction notes

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