Acetic Acid → HCID 14302181, compound

HRID 867771Notes

Reaction equation

HRID 867771 reaction equation
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[CH3:13][CH:14]([CH2:20][CH2:21][CH3:22])[CH2:15][C:16](OC)=[O:17].C(O)(=O)C>C1COCC1.O>[CH3:13][C@@H:14]([CH2:20][CH2:21][CH3:22])[CH2:15][C:16](=[O:17])[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 11535583HCID 11535583, compoundHCID 178418339Butyllithium

Product 1

HCID 14302181HCID 14302181, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon atmosphere, 1.63N n-butyl lithium (65 ml, 106 mmol) was added dropwise at -78° C. to a stirred solution of dimethyl methylphosphonate (13.6 g, 110 mmol) in anhydrous THF (200 ml) and stirring was further continued for 20 minutes. A solution of methyl l-3-methylhexanoate (6.92 g, 48 mmol) in anhydrous THF (20 ml) was added dropwise, and the mixture was stirred at room temperature for one hour. Acetic acid (6.7 ml) was added to neutralize the solution and water (70 ml) was then added. After concentration, the residue was extracted with ether (200 ml×2), and the combined organic layers were washed with brine (40 ml×2), and dried over anhydrous sodium sulfate. Concentration and purification by vacuum distillation gave dimethyl 4(S)-methyl-2-oxo-heptylphosphonate (8.18 g, 34.6 mmol, 72%, b.p.: 114°-115° C./0.25 mmHg).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. additionwas then added
  3. concentrationAfter concentration
  4. extractionthe residue was extracted with ether (200 ml×2)
  5. washthe combined organic layers were washed with brine (40 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration and purification
  8. distillationby vacuum distillation

Sources & evidence

ORD record
ord-c430ba09c6ef4e0ab8935f13a98f6763
Source dataset
uspto-grants-1988_10
Patent number
US04775692

Reaction notes

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