Chlorotrimethylsilane → 8-Trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

HRID 2601

Reaktionsgleichung

Reaktionsgleichung von HRID 2601
[CH3:1][C:2]1([CH3:16])[S:6][C:5]2=[CH:7][C:8]3[S:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]=3[CH:13]=[C:4]2[O:3]1.C([Li])CCC.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[CH3:24][Si:23]([CH3:26])([CH3:25])[C:13]1[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[S:6][C:5]=2[CH:7]=[C:8]2[S:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]=12

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 187852282,2,6,6-Tetramethylbenzo[1,2-d:5,4-d']bis(1,3)oxathioleHCID 178418339Butyllithium

Produkt 1

HCID 187852378-Trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The reaction was performed under an argon atmosphere using deoxygenated solvents. 2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole (6.0 g, 23.6 mmol) was dissolved in dry THF (120 mL). The mixture was cooled on an ice-bath and n-butyllithium (10.8 mL, 2.5M in hexane) was added dropwise over 10 min. After 15 min, chlorotrimethylsilane (6.0 mL, 47.2 mmol) was added dropwise over 5 min. After another 15 min, the reaction mixture was quenched with dietyl ether/aq. NaHCO3, the aqueous layer was extracted with ether and the combined organic layers were washed with water and dried (Na2SO4). After evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%) could be collected.

Aufarbeitung

  1. customusing deoxygenated solvents
  2. temperatureThe mixture was cooled on an ice-bath
  3. waitAfter another 15 min
  4. customthe reaction mixture was quenched with dietyl ether/aq
  5. extractionNaHCO3, the aqueous layer was extracted with ether
  6. washthe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
  9. customcould be collected

Quellen und Nachweise

ORD-Eintrag
ord-3fd18c20fe384f209c75449594a77dfc
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728370

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