Saccharin → N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharin

HRID 512019

Reaktionsgleichung

Reaktionsgleichung von HRID 512019
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C.O.CCOC(C)=O>[Si:23]([O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5](=[O:6])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:1]1(=[O:2])=[O:3])([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:25])[CH3:24]

Komponenten

7

Edukt 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Produkt 1

HCID 25018868N-(6-tert-Butyldimethylsilyloxy-hexyl)saccharinAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of saccharin (92 mg, 0.5 mmol) in anhydrous DMF (4 mL), at room temperature, under a nitrogen atmosphere, was added NaH (60% dispersion in mineral oil, 21 mg, 0.52 mmol). The mixture was stirred at the same temperature for additional 15 min, a solution of (6-bromohexyloxy)-tert-butyldimethylsilane (177 mg, 0.6 mmol) in DMF (1 mL) was added and the resulting mixture microwaved at 150° C. for 10 min. The reaction mixture was cooled to room temperature and diluted with water (5 mL) and AcOEt (10 mL). The organic layer was separated and the aqueous layer extracted with AcOEt (2×10 mL). The combined organic layer was washed with brine, dried (MgSO4) and the solvent removed in vacuum. The residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether) to give 83.8 (89 mg, 45% yield), as a viscous liquid.

Aufarbeitung

  1. customthe resulting mixture microwaved at 150° C. for 10 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer extracted with AcOEt (2×10 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuum
  7. customThe residue was purified by flash column chromatography on silica gel (20% ethyl acetate-petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-b27bcf4747144841a9e1fa95fccda40d
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102622B2

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