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

HRID 859123Notes

Reaction equation

HRID 859123 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].[CH:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])=O.CS(O)(=O)=O>C[O-].[Na+]>[O:12]=[C:11]1[O:13][CH:7]([P:1](=[O:6])([O:4][CH3:5])[O:2][CH3:3])[C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]1=2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8406Phthalaldehydic acidHCID 21884954Dimethylphosphite

Product 1

HCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Dimethyl phosphite (11 g, 0.1 mol) then 2-formylbenzoic acid (10.51 g, 0.07 mol) or equivalent were added dropwise at 0° C. under nitrogen to a stirred solution of sodium methoxide [from sodium (2.3 g) in methanol (80 ml)], the mixture was stirred at ambient temperature for 30 minutes, then it was quenched by the addition of methanesulphonic acid (10.6 g, 0.11 mol). The methanol was removed in vacuo, the residue was partitioned between dichloromethane (200 ml) and water (50 ml), then the dichloromethane solution was washed with water (2×50 ml) and dried (MgSO4). The solvent was removed in vacuo to leave dimethyl 3-oxobenzo[c]furan-1-ylphosphonate or equivalent.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residue was partitioned between dichloromethane (200 ml) and water (50 ml)
  3. washthe dichloromethane solution was washed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-07d4ba22b28a4048b7bb5180ea830740
Source dataset
uspto-grants-2006_12
Patent number
US07151102B2

Reaction notes

Loading…