Tetrahydrofuran → Dimethyl 2-Oxo-3-methylheptylphosphonate

HRID 918147Notes

Reaction equation

HRID 918147 reaction equation
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].O1CCCC1.[CH3:18][CH:19]([CH2:25][CH2:26][CH2:27][CH3:28])[C:20](OCC)=[O:21]>C(O)(=O)C>[O:21]=[C:20]([CH:19]([CH3:18])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonateHCID 12714009Ethyl 2-methylhexanoateHCID 178418339Butyllithium

Product 1

HCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

n-Butyllithium (150 ml.) is added slowly 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 racemic ethyl 2-methylhexanoate (18.4 g.) in 50 ml. of THF, and the resulting mixture is stirred at -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, 16.7 g., b.p. 126°-129° C./1 mm.

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-efd43842b5544df79cf43462e0791b7e
Source dataset
uspto-grants-1976_07
Patent number
US03969396

Reaction notes

Loading…