Reaktion #158285

Reaktionsgleichung

2-{[tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate

sodium iodide

→

title compound

Ausbeute 74.7%

tert-butyl [2-chloro-1-(iodomethyl)ethoxy]dimethylsilane

Ausbeute 74.7%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   workup.ADDITIONwater was added to the residue
3. 3
   Extraktionthe mixture was extracted with hexane
4. 4
   TrocknenThe extract was dried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To a mixture of 2-{[tert-butyl(dimethyl)silyl]oxy}-3-chloropropyl 4-methylbenzenesulfonate (20.3 g) in acetone (200 mL) was added sodium iodide (19.7 g), and the mixture was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, water was added to the residue, and the mixture was extracted with hexane. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.4 g).

Quelle