Sodium hydride → HCID 14031259, Verbindung

HRID 247376

Reaktionsgleichung

Reaktionsgleichung von HRID 247376
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>O1CCCC1.CN(C)C=O>[Si:17]([N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 67278Phenoxazine

Produkt 1

HCID 14031259HCID 14031259, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

5 Grams of phenoxazine was dissolved in 100 ml of dry tetrahydrofuran, then 1.63 g of 50% sodium hydride in mineral oil was added and the mixture refluxed for 30 minutes. Then 6.19 g of t-butyldimethylsilyl chloride in dimethylformamide (2 ml) and tetrahydrofuran (8 ml) was added and reflux was continued for five more minutes. The reaction was quenched by the addition of water, the organic layer was separated and dried over sodium sulfate. Then the solvent was removed under reduced pressure and the residue purified by column chromatography (silica as solid phase, hexane:ethylacetate (95:5) as mobile phase). N-t-butyldimethylsilylphenoxane had a melting point of 57° C. after crystallization from pentane.

Aufarbeitung

  1. temperaturethe mixture refluxed for 30 minutes
  2. temperaturereflux
  3. customThe reaction was quenched by the addition of water
  4. customthe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThen the solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography (silica as solid phase, hexane:ethylacetate (95:5) as mobile phase)
  8. customafter crystallization from pentane

Quellen und Nachweise

ORD-Eintrag
ord-ff27321f287a4e1ead576b4f6dfe71a7
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04707473

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