Methanol → HCID 68707308, compound

HRID 2097564Notes

Reaction equation

HRID 2097564 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][C:24](=[O:34])[CH2:25][C:26]3[CH:31]=CC(O)=[C:28]([OH:33])[CH:27]=3)[N:22]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17].C[OH:36].N1[CH:42]=[CH:41]C=CC=1>>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:18]2[S:19][CH:20]=[C:21]([CH2:23][C:24](=[O:34])[CH2:25][C:26]3[CH:31]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[C:28]([O:33][C:41](=[O:36])[CH3:42])[CH:27]=3)[N:22]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68711506HCID 68711506, compound

Product 1

HCID 68707308HCID 68707308, compoundYield 54%

Procedure

Acetic anhydride (2 ml, 20 mmol) was added dropwise at room temperature to a solution (4 ml) of 3-[2-(3,4-dimethoxyphenyl)thiazole-4-yl]-1-(3,4-dihydroxyphenyl)propanone (320 mg, 0.78 mmol) in pyridine at room temperature, followed by stirring at the same temperature for 1 hour. Methanol (10 ml) was added to the reaction mixture, stirring was carried out at room temperature for 1 hour, and the solvent was distilled off under reduced pressure. Subsequently, water was added, and extraction with ethyl acetate was performed. The residue was purified by silica gel column chromatography (eluent: ethyl acetate). The solvent was distilled off under reduced pressure, and the residue was recrystallized from an ethyl acetate/n-hexane mixed solvent, to thereby obtain 195 mg (yield: 54%) of 3-[2-(3,4-dimethoxyphenyl)thiazole-4-yl]-1-(3,4-diacetoxyphenyl)propanone as colorless needles.

Workup

  1. stirringstirring
  2. waitwas carried out at room temperature for 1 hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionSubsequently, water was added
  5. extractionextraction with ethyl acetate
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was recrystallized from an ethyl acetate/n-hexane mixed solvent

Sources & evidence

ORD record
ord-bda40c3896b64ace8633ad69f4c7cc6b
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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