HCID 69947162, compound → HCID 22898672, compound

HRID 1018513Notes

Reaction equation

HRID 1018513 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]([C:28]([F:31])([F:30])[F:29])[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>C(Cl)Cl>[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]([C:28]([F:31])([F:29])[F:30])[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

4

Reactant 2

HCID 69947162HCID 69947162, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22898672HCID 22898672, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 12 g (0.027 mol) of 2,6-dimethyl-4-(3-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester, obtained as described in A), and 98 g (0.082 mol) of pyridinium chlorochromate adsorbed on alumina, was suspended in 270 ml of CH2Cl2, and the suspension was maintained under stirring at room temperature for 6 hours. The remaining solid was eliminated by filtration, and the liquid was washed with water (3×300 ml), drive 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 65%.

Workup

  1. customobtained
  2. temperaturethe suspension was maintained
  3. filtrationThe remaining solid was eliminated by filtration
  4. washthe liquid was washed with water (3×300 ml), drive over anh. Na2SO4
  5. concentrationconcentrated at reduced pressure, to dryness
  6. customThe product was obtained as an oil, which
  7. customwas purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 65%

Sources & evidence

ORD record
ord-c80eb2fac5a2421380d929e13462dbd8
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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