Reaktion #44488

Reaktionsgleichung

NH4Cl

Sodium bis(trimethylsilyl)amide

tert-butyl-chloro-dimethyl-silane

cyclooctane-1,5-diol

→

title compound

5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanol

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGstirred for another thirty minutes
3. 3
   TemperaturThe solution was re-cooled (0° C.)
4. 4
   TemperaturThe solution was then warmed to room temperature
5. 5
   workup.ADDITIONwas added
6. 6
   SonstigeThe mixture was partitioned with diethyl ether
7. 7
   Waschenthe organic phase was washed with brine
8. 8
   Trocknendried (MgSO4)
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated
11. 11
    SonstigeThe residue was purified over silica gel using 2-40% ethyl acetate in hexanes

Vorschrift

Sodium bis(trimethylsilyl)amide (76.27 mL, 1 M in tetrahydrofuran, 76.27 mmol) was added drop wise to a stirred and cooled (0° C.) solution of cyclooctane-1,5-diol (10 g, 69.34 mmol) in dry tetrahydrofuran (120 mL). After the addition, the resulting solution was warmed to room temperature and stirred for another thirty minutes. The solution was re-cooled (0° C.) and a solution of tert-butyl-chloro-dimethyl-silane (10.45 g, 69.34 mmol) in tetrahydrofuran (20 mL) was added drop wise. The solution was then warmed to room temperature and stirred overnight before an NH4Cl solution was added. The mixture was partitioned with diethyl ether, and the organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 2-40% ethyl acetate in hexanes to provide the title compound as an oil.

Quelle