Hydrochloric Acid → 6-(6-carboxybenzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

HRID 1357210Notes

Reaction equation

HRID 1357210 reaction equation
C([O:4][C:5]1[C:10]([CH3:11])=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[C:19]([C:21]([O:23]C)=[O:22])[CH:18]=[CH:17][C:15]=3[CH:16]=2)[O:8][C:7](=[O:25])[C:6]=1[CH3:26])(=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO.O>[C:21]([C:19]1[CH:18]=[CH:17][C:15]2[CH:16]=[C:12]([C:9]3[O:8][C:7](=[O:25])[C:6]([CH3:26])=[C:5]([OH:4])[C:10]=3[CH3:11])[O:13][C:14]=2[CH:20]=1)([OH:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 185055404-acetyloxy-3,5-dimethyl-6-(6-(methoxycarbonyl)benzofuran-2-yl)-2H-pyran-2-one

Product 1

HCID 546827716-(6-carboxybenzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixed solution of 4-acetyloxy-3,5-dimethyl-6-(6-(methoxycarbonyl)benzofuran-2-yl)-2H-pyran-2-one (85 mg) and K2CO3 (45 mg) in MeOH (5 ml) and H2O (1 ml) was stirred at room temperature for one hour, and then the reaction solution was rendered acidic with a 1 N hydrochloric acid aqueous solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/MeOH=5/1) to obtain 6-(6-carboxybenzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (AcOEt/MeOH=5/1)

Sources & evidence

ORD record
ord-2bf419492e794606a5eea80949e59d93
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

Loading…