Dichloromethane → 5-(4-Hydroxybenzyl)-3-trityloxazolidine-2,4-dione

HRID 1595480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1595480
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]2[O:33][C:32](=[O:34])[NH:31][C:30]2=[O:35])=[CH:24][CH:23]=1.ClCCl>O.C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:31]2[C:30](=[O:35])[CH:29]([CH2:28][C:25]3[CH:26]=[CH:27][C:22]([OH:21])=[CH:23][CH:24]=3)[O:33][C:32]2=[O:34])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 3

HCID 6344DichloromethaneHCID 6456Trityl chlorideHCID 103529685-([4-Hydroxyphenyl]methyl)oxazolidine-2,4-dione

Produkt 1

HCID 149136625-(4-Hydroxybenzyl)-3-trityloxazolidine-2,4-dioneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

0.33 g (1.18 mmole) triphenylmethyl chloride was added to a solution of 0.245 g (1.18 mmole) 5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione, 0.165 ml (1.18 mmole) triethylamine, 5 ml dichloromethane and 5 ml dimethylformamide on an icebath. The temperature of the reaction mixture was allowed to reach room temperature. After 1.5 hours 0.05 ml more triethylamine was added. After 2 hours ethyl acetate and water were added and the phases were seperated. The organic phase was dried (sodium sulfate), the solvent was evaporated and the crude product was purified by chromatography on silica gel using heptane:ethyl acetate (3:2) as eluent to give 0.32 g (yield 60%) 3-triphenylmethyl-5-([4-hydroxyphenyl]methyl)oxazolidine-2,4-dione.

Aufarbeitung

  1. customto reach room temperature
  2. customthe phases were seperated
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. customthe solvent was evaporated
  5. customthe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-2e8117331b8542f9ad8c12deb457a29f
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06288096B1

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