Diethyl vinylphosphonate → Diethyl 2-(4-Benzoyloxy-2,2,6,6-tetramethylpiperidin-1-oxy)ethylphosphonate

HRID 2051080Notes

Reaction equation

HRID 2051080 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:15][CH:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[N:19]([OH:24])[C:18]([CH3:26])([CH3:25])[CH2:17]1)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:27]([P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[CH2:28]>O1CCCC1>[C:7]([O:15][CH:16]1[CH2:17][C:18]([CH3:26])([CH3:25])[N:19]([O:24][CH2:28][CH2:27][P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])[C:20]([CH3:22])([CH3:23])[CH2:21]1)(=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 69629Diethyl vinylphosphonateHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 19834292Diethyl 2-(4-Benzoyloxy-2,2,6,6-tetramethylpiperidin-1-oxy)ethylphosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.12 gram of potassium tert-butoxide in 25 ml of dry tetrahydrofuran is added 3.0 grams of 4-benzoyloxy-1-hydroxy-2,2,6,6-tetramethylpiperidine. After stirring the solution under nitrogen at room temperature for ten minutes, 1.78 grams of diethyl vinylphosphonate are added. After stirring the reaction mixture at room temperature under nitrogen for 24 hours, the solvent is removed under reduced pressure. The residue is partitioned between water and methylene chloride. The organic phase is washed with water, then brine and finally dried over anhydrous magnesium sulfate followed by evaportion. Purification of the residue by liquid chromatography affords the title compound as a colorless liquid. Analysis by nmr, ir and ms gives data consistent with the structure of the title compound.

Workup

  1. stirringAfter stirring the reaction mixture at room temperature under nitrogen for 24 hours
  2. customthe solvent is removed under reduced pressure
  3. customThe residue is partitioned between water and methylene chloride
  4. washThe organic phase is washed with water
  5. dry with materialbrine and finally dried over anhydrous magnesium sulfate
  6. customPurification of the residue by liquid chromatography

Sources & evidence

ORD record
ord-fd8207eef9d7489aa9e11be9af00da22
Source dataset
uspto-grants-1991_05
Patent number
US05015678

Reaction notes

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