2,6-Lutidine → HCID 86125527, compound

HRID 853645Notes

Reaction equation

HRID 853645 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8]O)(=[O:6])[O:4][CH3:5].N1C(C)=CC=CC=1C.[F:18][C:19]([F:32])([F:31])[S:20]([O:23]S(C(F)(F)F)(=O)=O)(=[O:22])=[O:21]>ClCCl>[CH3:1][O:2][P:3]([CH:7]([O:23][S:20]([C:19]([F:32])([F:31])[F:18])(=[O:22])=[O:21])[CH3:8])([O:4][CH3:5])=[O:6]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2733833Dimethyl (2-hydroxyethyl)phosphonate

Product 1

HCID 86125527HCID 86125527, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of (2-hydroxy-ethyl)-phosphonic acid dimethyl ester (0.250 g, 1.62 mmol) in dichloromethane (4 mL) was added 2,6-lutidine (0.284 mL, 2.44 mmol). The reaction mixture was cooled to −40° C. and trifluoromethanesulfonic anhydride (0.355 mL, 2.11 mmol) was added. The mixture stirred in the cold bath under an inert atmosphere for 2 hours at which point the reaction was completed as shown by 31P NMR (CDCl3) δ 25.7. The mixture was partitioned between dichloromethane and water both cooled by an ice-water bath. The organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo to afford trifluoromethanesulfonic acid dimethoxy-phosphoryl-2-ethyl ester 185 as an oil which was immediately carried forward with no further purification or characterization.

Workup

  1. customThe mixture was partitioned between dichloromethane and water
  2. temperatureboth cooled by an ice-water bath
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e6cfb62fc414487a05defc5b910e1c5
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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