Tetrahydrofuran → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

HRID 866691Notes

Reaction equation

HRID 866691 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].O1CCCC1.C([Li])CCC.[C:18](OCC)(=[O:27])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)(=O)C>[O:27]=[C:18]([CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonateHCID 16237Ethyl 3-phenylpropionateHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of dimethyl methylphosphonate (115.5 g.) in 2.1 l. of tetrahydrofuran is treated, while stirring at -65° C., with a solution of butyl lithium (660 ml. 1.6 M. in hexane). A solution of ethyl hydrocinnamate (93.5 g.) in 225 ml. of tetrahydrofuran is added at -65° C. Stirring is continued at -65° C. for 2 hrs. and then at about 25° C. for 16 hrs. Acetic acid (70 ml.) is added and the mixture concentrated under reduced pressure. The residue is partitioned between dichloromethane and water. The organic phase is dried and concentrated. Distillation yields the title compound, b. 188°-191° C./2 mm., having a mass spectral peak at 256.

Workup

  1. waitand then at about 25° C. for 16 hrs
  2. concentrationthe mixture concentrated under reduced pressure
  3. customThe residue is partitioned between dichloromethane and water
  4. customThe organic phase is dried
  5. concentrationconcentrated
  6. distillationDistillation

Sources & evidence

ORD record
ord-20629563b1164fa1b11cb9d8ec7779cb
Source dataset
uspto-grants-1978_07
Patent number
US04100355

Reaction notes

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