Acetic Acid → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

HRID 1288217Notes

Reaction equation

HRID 1288217 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.C([O:15][C:16](=O)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.C(O)(=O)C>O1CCCC1.CCCCCC>[O:15]=[C:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12958Dimethyl methylphosphonateHCID 16237Ethyl 3-phenylpropionateHCID 178418339Butyllithium

Product 1

HCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of dimethyl methylphosphonate (115.5 g.) in tetrahydrofuran (2.1 l.) at -65°, there is added 660 ml. of a 1.6 M solution of n-butyl lithium in hexane, and then there is added a solution of ethylhydrocinnamate (93.5 g.) in tetrahydrofuran (225 ml.). The mixture is stirred at -65° for 2 hrs. and then stirring is continued at 25° for 16 hrs. Acetic acid (70 ml.) is added, the solution is concentrated under reduced pressure and the residue is partitioned between methylene chloride and water. The organic layer is dried, concentrated, and distilled at 2 mm. to give 121.5 g. of the title compound; b.p. 184-195; mass spectrum 256 (M+).

Workup

  1. stirringand then stirring
  2. waitis continued at 25° for 16 hrs
  3. concentrationthe solution is concentrated under reduced pressure
  4. customthe residue is partitioned between methylene chloride and water
  5. customThe organic layer is dried
  6. concentrationconcentrated
  7. distillationdistilled at 2 mm
  8. customto give 121.5 g

Sources & evidence

ORD record
ord-25d24f4f636e4f1197f5ff13bec07f71
Source dataset
uspto-grants-1976_10
Patent number
US03987087

Reaction notes

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