Methanesulfonic Acid → Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

HRID 886982Notes

Reaction equation

HRID 886982 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].C[O-].[Na+].[C:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=O)([OH:12])=[O:11].CS(O)(=O)=O>CO>[CH3:3][O:2][P:1]([CH:15]1[C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10](=[O:12])[O:11]1)(=[O:6])[O:4][CH3:5]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8406Phthalaldehydic acidHCID 10942334Sodium MethoxideHCID 21884954Dimethylphosphite

Product 1

HCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

Dimethyl phosphite was added drop-wise to a solution of sodium methoxide in methanol at 0° C. 2-Carboxybenzaldehyde (H) was then added portion-wise to the reaction mixture as a slurry in methanol, with the temperature kept below 5° C. The resulting pale yellow solution was warmed to 20° C. over 1 hour. Methanesulphonic acid was added to the reaction drop-wise and the resulting white suspension was evaporated in vacuo. The white residue was quenched with water and extracted into chloroform. The combined organic extracts were washed with water, dried over MgSO4, and evaporated in vacuo to yield (3-oxo-1,3-dihydro-isobenzofuran-1-yl) phosphonic acid dimethyl ester (G) as a white solid (yield: 95%). This was then used without further purification in the next stage.

Workup

  1. customkept below 5° C
  2. customthe resulting white suspension was evaporated in vacuo
  3. customThe white residue was quenched with water
  4. extractionextracted into chloroform
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-93638b84d18347209140f86b655ac134
Source dataset
uspto-grants-2012_08
Patent number
US08247416B2

Reaction notes

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