Diethyl [difluoro(4-formylphenyl)methyl]phosphonate → HCID 53775855, compound

HRID 581695Notes

Reaction equation

HRID 581695 reaction equation
[CH2:1]([O:3][P:4]([C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CC(C)=[O:22].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([O:3][P:4]([C:9]([F:19])([F:18])[C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:22])=[O:17])=[CH:12][CH:11]=1)([O:5][CH2:6][CH3:7])=[O:8])[CH3:2]

Participants

4

Reactant 2

HCID 54474068Diethyl [difluoro(4-formylphenyl)methyl]phosphonateHCID 131709961Jones' reagent

Product 1

HCID 53775855HCID 53775855, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of [Difluoro-(4-formyl-phenyl)-methyl]-phosphonic acid diethyl ester (260 mg, 0.9 mmol) in acetone (25 mL) at room temperature was added Jones reagent (5 mL). The reaction was quenched by addition of ethanol (5 mL). The reaction was then concentrated under reduced pressure to 5 mL. The residue was diluted with ethyl acetate and washed with water (2×20 mL), saturated sodium chloride (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a white crystalline solid (268 mg, 98%). 1H NMR (400 MHz, DMSO): δ 8.09 (d, 2H), 7.70 (d, 2H), 4.15 (m, 4H), 1.22 (t, 6H); Mass Spectrum (Chemical Ionization, 1% NH in CH4) m/z 309 (M+H).

Workup

  1. customThe reaction was quenched by addition of ethanol (5 mL)
  2. concentrationThe reaction was then concentrated under reduced pressure to 5 mL
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water (2×20 mL), saturated sodium chloride (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80c519d93a454398ad8491cd38d089ff
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

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