Phosphorus oxychloride → HCID 21838046, compound

HRID 1740301Notes

Reaction equation

HRID 1740301 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([C:25]2[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])=[CH:17]1.C([O-])(=O)C.[Na+]>CNC=O>[CH:14]([C:17]1[O:16][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]=1[C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=1)[C:28]([O:30][CH3:31])=[O:29])=[O:15]

Participants

6

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 517045Sodium AcetateHCID 21838245HCID 21838245, compound

Product 1

HCID 21838046HCID 21838046, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 31254N-MethylformamideSolvent

Procedure

To a mixture of phosphorus oxychloride (3 g) and N-methylformanilide (3 g) was added a solution of methyl 3-(benzofuran-3-yl)benzoate (3 g) in N-methylformamide (1.5 g) at room temperature. The mixture was stirred overnight at room temperature and was poured onto aqueous sodium acetate solution. The product was extracted with ethyl acetate and the organic layer was washed with hydrochloric acid solution, water and brine. The layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1) to afford methyl 3-(2-formylbenzofuran-3-yl)benzoate (2.39 g).

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe organic layer was washed with hydrochloric acid solution, water and brine
  3. dry with materialThe layer was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0918518a26ae459bbad7f4008c9808e8
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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