Chlorotrimethylsilane → N-(2,6-Dimethylbenzyl)phthalimide

HRID 25027

Reaktionsgleichung

Reaktionsgleichung von HRID 25027
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4]O.Cl[Si](C)(C)C.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CS(C)=O.CN(C=O)C.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[CH2:4][N:20]1[C:16](=[O:26])[C:17]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:18]2[C:19]1=[O:21]

Komponenten

8

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 186748(2,6-Dimethylphenyl)methanolHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 10825581N-(2,6-Dimethylbenzyl)phthalimide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2,6-Dimethylbenzyl Alcohol (Step A, 6.59 g, 48.4 mmol) in DMSO (20 ml) was added chlorotrimethylsilane (15.75 ml, 145 mmol) at room temperature, and the mixture was stirred for one hr. To this reaction mixture were added ethyl acetate and water, the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give an oil. The oily residue was redissolved in DMF (100 ml) and potassium phthalimide (10.76 g, 58.1 mmol) was added. The reaction mixture was stirred for 16 hours at room temperature, ethyl acetate was added, and the organic layer was washed with 3% Na2CO3, 1 N HCl, dried over Na2SO4, filtered and concentrated to give white solid. The purification was done by flash chromatography on silica gel column (chloroform:methanol 95:5) to provide the title compound as white solid.

Aufarbeitung

  1. washthe organic layer was washed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give an oil
  6. stirringThe reaction mixture was stirred for 16 hours at room temperature
  7. washthe organic layer was washed with 3% Na2CO3, 1 N HCl
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give white solid
  12. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-b39a908e70c044be99ef9823cba1f34d
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858602B2

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