1,4-Dioxane → HCID 18505628, compound

HRID 1357204Notes

Reaction equation

HRID 1357204 reaction equation
[CH3:1][C:2]1[C:3](=[O:25])[O:4][C:5]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:16]=3[CH:17]=2)=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11].[H][H].O1CCO[CH2:30][CH2:29]1>CCO.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:15]2[O:14][C:13]([C:5]3[O:4][C:3](=[O:25])[C:2]([CH3:1])=[C:7]([O:8][CH2:9][O:10][CH3:11])[C:6]=3[CH3:12])=[CH:17][C:16]=2[CH:18]=1.[CH3:1][C:2]1[C:3](=[O:25])[O:4][C:5]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][C:19]([NH:22][CH2:29][CH3:30])=[CH:18][C:16]=3[CH:17]=2)=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11]

Participants

7

Reactant 3

HCID 312751,4-DioxaneHCID 18505697HCID 18505697, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 18505628HCID 18505628, compoundHCID 18505905HCID 18505905, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3,5-dimethyl-4-methoxymethoxy-6-(5-nitrobenzofuran-2-yl)-2H-pyran-2-one (100 mg) in dioxane (20 ml) and EtOH (20 ml) there was added 5% Pd/C (5 mg), and after displacing the reaction vessel atmosphere with hydrogen, the mixture was stirred at room temperature overnight. The reaction solution was filtered and concentrated, and then purified by silica gel thin-layer chromatography (n-hexane/AcOEt=1/1) to obtain 6-(5-aminobenzofuran-2-yl)-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one and 3,5-dimethyl-6-(5-(ethylamino)benzofuran-2-yl)-4-methoxymethoxy-2H-pyran-2-one.

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel thin-layer chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-09125c12b22c48e695410d95ac9a61d5
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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