Ethyl heptanoate → Dimethyl (2-oxooctyl)phosphonate

HRID 66242Notes

Reaction equation

HRID 66242 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].O1CCCC1.[C:13](OCC)(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(O)(=O)C>[O:20]=[C:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

5

Reactant 3

HCID 7797Ethyl heptanoateHCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonate

Product 1

HCID 13390134Dimethyl (2-oxooctyl)phosphonate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

n-Butyllithiium (130 ml. of 1.6 M. solution) is slowly added to a solution of dimethyl methylphosphonate (25.6 g.) in 475 ml. of tetrahydrofuran (THF) at about -65° C. To the mixture is added a solution of ethyl heptanoate (18.4 g.) in 50 ml. of THF, annd the resulting mixture is stirred at about -70° C. for 2 hrs. Then, 16 ml. of acetic acid is added, and the mixture is concentrated under reduced pressure. The residue is mixed with dichloromethane (about 400 ml.) and water (about 50 ml.) shaken, and separated. The organic phase is dried over magnesium sulfate and concentrated. Distillation yields the title compound.

Workup

  1. customat about -65° C
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionThe residue is mixed with dichloromethane (about 400 ml.) and water (about 50 ml.)
  4. customseparated
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationDistillation

Sources & evidence

ORD record
ord-c2faf03a3fe7473386599f958ca774fd
Source dataset
uspto-grants-1978_12
Patent number
US04130721

Reaction notes

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