Acetic Acid → HCID 14302173, compound

HRID 867760Notes

Reaction equation

HRID 867760 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[CH3:13][C:14]([CH3:25])([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:15](OC)=[O:16].C(O)(=O)C>C1COCC1.O>[CH3:13][C:14]([CH3:25])([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 84291Methyl 2,2-dimethyloctanoateHCID 178418339Butyllithium

Product 1

HCID 14302173HCID 14302173, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Dimethyl methylphosphonate (7.6 g, 0.061 mol) was dissolved in 70 ml anhydrous THF under argon atmosphere. To the mixture stirred at -78° C. was added dropwise n-butyl lithium (1.44N, 42.4 ml, 0.061 mol). After 30 minutes, methyl 2,2-dimethyloctanoate (4.5 g, 0.024 mol) was further added dropwise. After being stirred for 30 minutes the mixture was warmed to room temperature. To the mixture cooled with ice bath were added 3.8 ml of acetic acid and 10 ml of water. After concentration of the reaction mixture, 20 ml of water was added to the residue and the mixture was extracted with ethyl acetate (50 ml×2). The ethyl acetate layers were washed with water (20 ml×1) and with brine (20 ml×1), dried over anhydrous sodium sulfate, and concentrated. Distillation of the residue gave dimethyl 3,3-dimethyl-2-oxononanylphosphonate (5.34 g, 0.0192 mol, 79%, b.p. 137° -140° C./0.6 mmHg). The structure of this product was confirmed by the following data.

Workup

  1. stirringAfter being stirred for 30 minutes the mixture
  2. temperaturewas warmed to room temperature
  3. temperatureTo the mixture cooled with ice bath
  4. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  5. washThe ethyl acetate layers were washed with water (20 ml×1) and with brine (20 ml×1)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. distillationDistillation of the residue

Sources & evidence

ORD record
ord-244ef31ab5e14349bd81135bbf025f83
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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