Acetic Acid → Dimethyl (4-ethoxy-3,3-dimethyl-2-oxobutyl)phosphonate

HRID 460928Notes

Reaction equation

HRID 460928 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])[CH2:9][CH2:10][CH3:11].[C:13](O)(=[O:15])C.[O:17]1[CH2:21][CH2:20]C[CH2:18]1>CCCCCC>[O:15]=[C:13]([C:10]([CH3:9])([CH3:11])[CH2:18][O:17][CH2:21][CH3:20])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonateHCID 178418339Butyllithium

Product 1

HCID 14302195Dimethyl (4-ethoxy-3,3-dimethyl-2-oxobutyl)phosphonate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

18 g of dimethyl methylphosphonate in 100 ml of tetrahydrofurane were cooled under argon to -70° C. 100 ml of a 2-molar n-butyl-lithium solution in hexane are added dropwise with stirring. After 15 minutes, 20 g of 1,1-dimethyl-2-ethoxy-propionic acid methyl ester in 75 ml of tetrahydrofurane were added dropwise at -70° C. The mixture was then stirred for 2 hours. It was neutralised with 12 ml of glacial acetic acid. The solvent was concentrated (sic) in vacuo, the residue was taken up in chloroform and washed with water and the chloroform phase was dried with MgSO4 and concentrated and the residue was distilled in vacuo.

Workup

  1. stirringThe mixture was then stirred for 2 hours
  2. concentrationThe solvent was concentrated (sic) in vacuo
  3. washwashed with water
  4. dry with materialthe chloroform phase was dried with MgSO4
  5. concentrationconcentrated
  6. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-72f3f622e0f6467fba9aacc2af4b3e89
Source dataset
uspto-grants-1977_12
Patent number
US04061671

Reaction notes

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