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Methanol → 5-[[4-[[(4E)-6-hydroxy-4-hydroxyimino-2,5,7,8-tetramethyl-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

HRID 1030362
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Reaktionsgleichung

Reaktionsgleichung von HRID 1030362
[OH:1][C:2]1[C:3]([CH3:32])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:30]=[CH:29][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:19][CH:18]=1)([CH3:14])[CH2:6][C:5]2=O.Cl.[NH2:34][OH:35].CO.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.N1C=CC=CC=1>[OH:1][C:2]1[C:3]([CH3:32])=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[O:8][C:7]([CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][CH:22]3[S:26][C:25](=[O:27])[NH:24][C:23]3=[O:28])=[CH:29][CH:30]=1)([CH3:14])[CH2:6]/[C:5]/2=[N:34]\[OH:35]
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Komponenten

7

Edukt 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 98252415-[4-(6-Hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Produkt 1

HCID 883935005-[[4-[[(4E)-6-hydroxy-4-hydroxyimino-2,5,7,8-tetramethyl-3H-chromen-2-yl]methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5 g of 5-[4-(6hydroxy-2,5,7,8-tetramethyl-4-oxochroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 22 of copending U.S. Ser. No. 644,996), 3 g of hydroxylamine hydrochloride, 50 g of methanol and 3 g of pyridine was stirred for 1 week at room temperature. At the end of this time, ethyl acetate and an aqueous solution of potassium carbonate were added. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was purified by silica gel column chromatography, eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to give the title compound, softening at 84°-100° C.

Aufarbeitung

  1. customprepared
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography
  6. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-2ebe627fbe2c4553b26ff6a19de08a3c
Quelldatensatz
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05104888

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