HCID 5178648, compound → HCID 22898683, compound

HRID 1018518Notes

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][C:25]([Cl:28])=[C:24]([N+:29]([O-:31])=[O:30])[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][C:25]([Cl:28])=[C:24]([N+:29]([O-:31])=[O: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

Reactant 2

HCID 5178648HCID 5178648, compound

HCID 178418287HCID 178418287, compound

Product 1

HCID 22898683HCID 22898683, compoundYield 69%

Procedure

A mixture of 9 g (0.020 mol) of 4-(4-chloro-3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester 5-(tetrahydrofuran-2-ylmethyl) ester, obtained as described in A) in 72 g (0.060 mol) of pyridinium chlorochromate adsorbed on alumina, were suspended on 200 ml of CH2C12 then, the mixture was maintained with stirring at room temperature for 9 hours. The remaining solid was filtered, and the filtrate was washed with water (3×200 ml), dried with anh. Na2SO4, and the solvent evaporated under reduced pressure. The product was isolated as an oil, which was purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 69%.

Workup

customobtained
temperaturethe mixture was maintained
filtrationThe remaining solid was filtered
washthe filtrate was washed with water (3×200 ml)
dry with materialdried with anh. Na2SO4
customthe solvent evaporated under reduced pressure
customThe product was isolated as an oil, which
customwas purified by column chromatography (Silicagel, n-hexane:EtAcO, 8:2) with a yield of 69%

Sources & evidence

ORD record: ord-1a72120bf477478f866c08b1a1761629
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482841B1

Reaction notes

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