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

HRID 640687Notes

Reaction equation

HRID 640687 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-52677ffd4b3e42379b4a9f613d5661fd
Source dataset
uspto-grants-2010_04
Patent number
US07692006B2

Reaction notes

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