Methanol → HCID 18707143, compound

HRID 1421985Notes

Reaction equation

HRID 1421985 reaction equation
CO.[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[C:24]([CH2:26][CH:27]=[CH2:28])[C:23]([OH:29])=[C:22]([C:30]([O:32][CH3:33])=[O:31])[CH:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4].O=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[C:22]([C:30]([O:32][CH3:33])=[O:31])[C:23]4[O:29][C:27]([CH3:28])=[CH:26][C:24]=4[CH:25]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

7

Reactant 3

HCID 887MethanolHCID 977OxygenHCID 18707312HCID 18707312, compound

Product 1

HCID 18707143HCID 18707143, compoundYield 23.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 167845palladium(II) acetateCatalyst3×HCID 962WaterSolvent

Procedure

In a mixed solvent consisting of 50 ml of methanol and 5 ml of water were suspended 1 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-allylphenyl)thiazole, 50 mg of palladium acetate [Pd(OAc)2 ] and 230 mg of copper acetate [Cu(OAc)2.H2O]. The suspension was stirred in an oxygen atmosphere at 50° C. for 6 hours. 50 mg of palladium acetate was further added. After 10 hours, 50 mg of palladium acetate was furthermore added. After 14 hours, when no solid starting materials in the reaction mixture were visible, the reaction mixture was filtered. The filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/1 by v/v) and recrystallized from methanol-dichloromethane to obtain 230 mg of 2-(3,4-diethoxyphenyl)-4-(2-methyl-7-methoxycarbonyl-5-benzofuryl)thiazole.

Workup

  1. waitAfter 14 hours
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/1 by v/v)
  5. customrecrystallized from methanol-dichloromethane

Sources & evidence

ORD record
ord-60a25ca032504fbf8ee9be563231fcd3
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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