Dimethyl methylphosphonate → Dimethyl (3-fluoro-2-oxoheptyl)phosphonate

HRID 1588412Notes

Reaction equation

HRID 1588412 reaction equation
[CH3:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4].C([Li])CCC.[F:13][CH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[C:15](OC)=[O:16]>C1COCC1>[F:13][CH:14]([CH2:19][CH2:20][CH2:21][CH3:22])[C:15](=[O:16])[CH2:1][P:2](=[O:7])([O:5][CH3:6])[O:3][CH3:4]

Participants

5

Reactant 3

HCID 12958Dimethyl methylphosphonateHCID 13706743HCID 13706743, compoundHCID 178418339Butyllithium

Product 1

HCID 13245337Dimethyl (3-fluoro-2-oxoheptyl)phosphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dimethyl methylphosphonate (8.38 g) was dissolved in dry THF (250 ml) and cooled to -78° C. n-Butyllithium (1.6-M, 42 ml) was added dropwise, and the reaction was stirred for 10 minutes. The above methyl fluorocaproate (200 g) in THF (10 ml) was added dropwise. After addition, the mixture was stirred at -78° C. for 45 minutes, and then at room temperature for additional 45 minutes. The crude product obtained after the conventional work-up was chromatographed (hexane/ethyl acetate=1/1). Yield; 5.04 g (62 g)

Workup

  1. additionwas added dropwise
  2. additionAfter addition
  3. stirringthe mixture was stirred at -78° C. for 45 minutes
  4. waitat room temperature for additional 45 minutes

Sources & evidence

ORD record
ord-dc693c990ce24177ace9f8ec025d1025
Source dataset
uspto-grants-1993_06
Patent number
US05221763

Reaction notes

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