Methyl iodide → Diethyl 2-diethylphosphono-2,4,4-trimethyladipate

HRID 1706647

Reaction equation

HRID 1706647 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([CH2:15][C:16]([CH3:24])([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H-].[Na+].[CH3:27]I>O1CCOCC1>[CH2:7]([O:6][P:4]([C:9]([CH3:27])([CH2:15][C:16]([CH3:24])([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53814271Diethyl 2-diethylphosphono-4,4-dimethyladipate

Product 1

HCID 53764006Diethyl 2-diethylphosphono-2,4,4-trimethyladipate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Diethyl 2-diethylphosphono-4,4-dimethyladipate (3.6 parts) (See Example 9) was added dropwise to a suspension of sodium hydride (0.6 parts, 50% in oil) in dry dioxan (100 parts by volume) containing methyliodide (14.2 parts) over 2 hr. at room temperature. The resulting solution was stirred at room temperature for 18 hr. then heated to reflux for 2 hr., cooled, the solids removed by filtration and the filtrate concentrated in vacuo. Distillation of the residual oil gave 3 parts of diethyl 2-diethylphosphono-2,4,4-trimethyladipate, boiling at 137°-8° C./0.03 mm having a 31P chemical shift of -26 ppm and having the following elemental analysis by weight.

Workup

  1. customat room temperature
  2. temperaturethen heated
  3. temperatureto reflux for 2 hr
  4. temperature, cooled
  5. customthe solids removed by filtration
  6. concentrationthe filtrate concentrated in vacuo
  7. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-46d4dbef5c744d3c876ec87e713a8e5b
Source dataset
uspto-grants-1980_06
Patent number
US04208344

Linked notes

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