Triethyl phosphonoacetate → HCID 54160597, compound

HRID 429733Notes

Reaction equation

HRID 429733 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6]P(OCC)(OCC)=O)=[O:5].[H-].[Na+].[C:17]([O:21][C:22](=[O:41])[N:23]([CH:25]([CH:39]=O)[CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:24])([CH3:20])([CH3:19])[CH3:18].S([O-])(O)(=O)=O.[K+]>O1CCCC1.O.C(OCC)(=O)C.CCCCC>[CH2:2]([O:3][C:4](=[O:5])[CH:6]=[CH:39][CH:25]([N:23]([C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:41])[CH3:24])[CH:26]([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:1]

Participants

9

Reactant 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 53882379HCID 53882379, compound

Product 1

HCID 54160597HCID 54160597, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 14 ml (68 mmol) of phosphonoacetic acid triethyl ester in 130 ml of tetrahydrofuran is added at 0C to a solution of 3.7 g (84 mmol) of 55-65% sodium hydride dispersion (washed three times with pentane) in 130 ml of tetrahydrofuran. After 1 hour a solution of 13.6 g (40 mmol) of (1-formyl-2,2-diphenyl-ethyl)-methyl-carbamic acid tert-butyl ester in 130 ml of tetrahydrofuran is added dropwise thereto. After 4 hours the reaction mixture is rendered neutral with 1M potassium hydrogen sulfate and then diluted with water and ethyl acetate. The organic phase is washed three times with water, dried over magnesium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel using methylene chloride/methanol (99:1 to 98:2). The title compound is obtained in the form of a yellow oil. TLC: methylene chloride/methanol (98:2) Rf=0.45.

Workup

  1. washThe organic phase is washed three times with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-e20d05f04f79490f951e52331c09e5c8
Source dataset
uspto-grants-2001_11
Patent number
US06319917B1

Reaction notes

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