HCID 69944501, compound → HCID 22898680, compound

HRID 1018515Notes

Reaction equation

HRID 1018515 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]#[N: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]#[N:29])[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 69944501HCID 69944501, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 22898680HCID 22898680, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g (0.025 mol) of 4-(3-cyanophenyl)-2,6-dimethyl 1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester, obtained as described in A), and 91 g (0.076 mol) of pyridinium chlorochromate adsorbed on alumina, was suspended on 250 ml of CH2Cl2, and the suspension was stirred at room temperature for 5 hours. The remaining solid was separated by filtration, and the organic solution was washed with water (3×150 ml), dried with anh. Na2SO4, and concentrated to dryness at reduced pressure. The product was obtained as an oil, which was purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 78%.

Workup

  1. customobtained
  2. customThe remaining solid was separated by filtration
  3. washthe organic solution was washed with water (3×150 ml)
  4. dry with materialdried with anh. Na2SO4
  5. concentrationconcentrated to dryness at reduced pressure
  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 78%

Sources & evidence

ORD record
ord-782d310e0e4d41c5bcc4a4048afd5e2f
Source dataset
uspto-grants-2002_11
Patent number
US06482841B1

Reaction notes

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