Acetic Acid → 3,5-dimethyl-4-hydroxy-6-(6-(methoxycarbonyl) benzofuran-2-yl)-2H-pyran-2-one

HRID 1357211Notes

Reaction equation

HRID 1357211 reaction equation
C[Si](C=[N+]=[N-])(C)C.[C:8]([C:11]1[CH:29]=[CH:28][C:14]2[CH:15]=[C:16]([C:18]3[O:23][C:22](=[O:24])[C:21]([CH3:25])=[C:20]([OH:26])[C:19]=3[CH3:27])[O:17][C:13]=2[CH:12]=1)([OH:10])=[O:9].[C:30](O)(=O)C>CO.C1(C)C=CC=CC=1>[CH3:25][C:21]1[C:22](=[O:24])[O:23][C:18]([C:16]2[O:17][C:13]3[CH:12]=[C:11]([C:8]([O:10][CH3:30])=[O:9])[CH:29]=[CH:28][C:14]=3[CH:15]=2)=[C:19]([CH3:27])[C:20]=1[OH:26]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 546827716-(6-carboxybenzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

Product 1

HCID 546827513,5-dimethyl-4-hydroxy-6-(6-(methoxycarbonyl) benzofuran-2-yl)-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyldiazomethane (2 M hexane solution, 85 μl) was added to a mixed solution of 6-(6-carboxybenzofuran-2-yl)-3,5-dimethyl-4-hydroxy-2H-pyran-2-one (50 mg) in MeOH (5 ml) and toluene (1 ml), and the mixture was stirred at room temperature for 10 minutes. After adding acetic acid to the reaction solution for quenching of the excess trimethylsilyldiazomethane, it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH =9/1) to obtain 3,5-dimethyl-4-hydroxy-6-(6-(methoxycarbonyl) benzofuran-2-yl)-2H-pyran-2-one.

Workup

  1. customfor quenching of the excess trimethylsilyldiazomethane, it
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH =9/1)

Sources & evidence

ORD record
ord-1d32e02aa24844eeb695d45744aea4a4
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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