Reaktion #2698

Reaktionsgleichung

NaHCO3

Sodium iodide

chlorotrimethylsilane

Tris-(8-trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol

→

Tris-(2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl) methanol

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONpoured onto diethyl ether/aq
2. 2
   ExtraktionThe aqueous layer was extracted with ether
3. 3
   Waschenthe combined organic layers were washed twice with water
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated
6. 6
   Sonstigechromatographed (silica gel; dichloromethane)
7. 7
   Sonstigefinally triturated with ethyl acetate
8. 8
   Sonstigeto yield the product as slightly brown crystals

Vorschrift

Tris-(8-trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiol-4-yl)methanol (0.62 g, 0.62 mmol) was dissolved in acetonitrile (150 mL). Sodium iodide (0.75 g, 6.0 mmol) and chlorotrimethylsilane (0.65 g, 6.0 mmol) was added in one portion. The mixture was stirred for 20 min and then poured onto diethyl ether/aq. NaHCO3. The aqueous layer was extracted with ether and the combined organic layers were washed twice with water, dried (Na2SO4), evaporated, chromatographed (silica gel; dichloromethane) and finally triturated with ethyl acetate to yield the product as slightly brown crystals.

Quelle