Water → HCID 15675232, compound

HRID 1090120Notes

Reaction equation

HRID 1090120 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([CH3:20])=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-:24])C.[K+].O=O.O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:10]=1[C:20](=[O:24])[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 977OxygenHCID 15675231HCID 15675231, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 15675232HCID 15675232, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Benzyloxy-5-methoxy-3-methylindole (3.5 g) was dissolved in dimethylformamide (40 ml), and potassium t-butoxide (3.3 g) was added to the mixture. The resulting mixture was stirred at room temperature under a stream of oxygen for 5 days, poured into water and extraction with ethyl acetate was conducted. The extract was washed with saturated saline and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Wako Gel C-200, 80 g). Elution with a mixed solvent of chloroform (92 parts) and methanol (8 parts) gave 5-benzyloxy-6-methoxy-4(1H)-quinolone (compound 4; 390 mg).

Workup

  1. washThe extract was washed with saturated saline
  2. dry with materialdried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Wako Gel C-200, 80 g)
  5. washElution with a mixed solvent of chloroform (92 parts) and methanol (8 parts)

Sources & evidence

ORD record
ord-b75dffa2398f4e98b12efc421f8df102
Source dataset
uspto-grants-1992_01
Patent number
US05081121

Reaction notes

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