Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate

HRID 1357191Notes

Reaction equation

HRID 1357191 reaction equation
[CH:1]([O-:5])([O-])[O:2][CH3:3].[CH3:6]C1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.C([C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:30][C:29]=2[CH:37]=1)=O>CO>[CH3:6][O:5][CH:1]([O:2][CH3:3])[C:25]1[CH:26]=[CH:27][C:28]2[O:32][C:31]([C:33]([O:35][CH3:36])=[O:34])=[CH:30][C:29]=2[CH:37]=1

Participants

5

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 12082974Methyl 5-formylbenzofuran-2-carboxylateHCID 53629101Methylorthoformate

Product 1

HCID 15462830Methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl orthoformate (1.0 g) and polymer-bound PPTS (1.0 g) were added to a solution of methyl 5-formylbenzofuran-2-carboxylate (15 g) in MeOH (100 ml), and after allowing the mixture to stand at room temperature for 8 hours, the reaction solution was filtered and the mother liquor was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1) to obtain methyl 5-(dimethoxymethyl)benzofuran-2-carboxylate.

Workup

  1. filtrationthe reaction solution was filtered
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1)

Sources & evidence

ORD record
ord-86ae9adc442c40918d6a98e1fba088c3
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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