Water → Diethyl 4-methyl-2oxa-pent-4-enylphosphonate

HRID 908103Notes

Reaction equation

HRID 908103 reaction equation
[OH:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[H-].[Na+].Cl[CH:14]=[C:15]([CH3:17])[CH3:16].O>C1COCC1>[CH3:16][C:15](=[CH2:14])[CH2:17][O:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 105551-Propene, 1-chloro-2-methyl-HCID 24758Sodium hydrideHCID 76513Diethyl phosphonomethanol

Product 1

HCID 11481447Diethyl 4-methyl-2oxa-pent-4-enylphosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl hydroxymethylphosphonate (3 g, 17.8 mmol, 1 eq) is dissolved in 50 ml of THF to which sodium hydride (0.43 g, 17.8 mmol, 1 eq) is added. 1-chloro-2-methylpropene (1.62 g, 17.8 mmol, 1 eq) is then added. After one hour under magnetic stirring, at ambient temperature and in a nitrogen atmosphere, hydrolysis is performed with 100 ml of water. Extraction is performed with ether (3×50 ml). The organic phases are collected, washed with 100 ml of a saturated sodium chloride solution and dried on sodium sulphate. After evaporation of the solvent, the residual oil obtained is purified by silica gel chromatography (Eluent=ethyl acetate).

Workup

  1. additionis added
  2. customat ambient temperature and in a nitrogen atmosphere, hydrolysis
  3. extractionExtraction
  4. customThe organic phases are collected
  5. washwashed with 100 ml of a saturated sodium chloride solution
  6. customdried on sodium sulphate
  7. customAfter evaporation of the solvent
  8. customthe residual oil obtained
  9. customis purified by silica gel chromatography (Eluent=ethyl acetate)

Sources & evidence

ORD record
ord-6e4e6cb529254826a7e63a332d72d9ee
Source dataset
uspto-grants-2011_09
Patent number
US08017596B2

Reaction notes

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