HCID 3290996, compound → HCID 22898679, compound

HRID 1018508Notes

Reaction equation

HRID 1018508 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[C:12]([C:18]([O:20][CH3:21])=[O:19])[C:13]([CH3:17])=[N:14][C:15]=1[CH3:16])=[O:9]

Participants

3

Reactant 2

HCID 3290996HCID 3290996, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22898679HCID 22898679, compoundYield 70%

Procedure

A mixture of 8 g (0.02 mol) de 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester, obtained according A), and 71 g (0.059 mol) of pyridinium chlorochromate absorbed on alumina, was suspended in 200 ml of CH2Cl2. Then, the whole mixture was maintained with stirring at room temperature, along 8 hours. The remaining solid was eliminated by filtration, and the liquid was washed with water (3×250 ml). dried over anh. Na2SO4, and concentrated at reduced pressure, to dryness. The product was obtained as an oil, which was purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 70%.

Workup

  1. customobtained
  2. customabsorbed on alumina
  3. temperatureThen, the whole mixture was maintained
  4. filtrationThe remaining solid was eliminated by filtration
  5. washthe liquid was washed with water (3×250 ml)
  6. dry with materialdried over anh. Na2SO4
  7. concentrationconcentrated at reduced pressure, to dryness
  8. customThe product was obtained as an oil, which
  9. customwas purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 70%

Sources & evidence

ORD record
ord-fd0beb1ff2f444bab7decbfdf412e0e3
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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