HCID 69945124, compound → HCID 22898676, compound

HRID 1018507Notes

Reaction equation

HRID 1018507 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]=[CH:24][C:23]=2[Cl:28])[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]=[CH:24][C:23]=2[Cl:28])=[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 69945124HCID 69945124, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22898676HCID 22898676, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8 g (0.02 mol) of 4-(2-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 adsorbed on alumina, was suspended in 200 ml of CH2Cl2, and the whole mixture was stirred at room temperature for 5 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 66%,

Workup

  1. customobtained
  2. filtrationThe remaining solid was eliminated by filtration
  3. washthe liquid was washed with water (3×250 ml)
  4. dry with materialdried 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 66%

Sources & evidence

ORD record
ord-d37b29532c914d80aa4fb0b786f03ce4
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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