Réaction #40337

Équation de réaction

Trimethyl-(4-phenyl-cyclohex-1-enyloxy)-silane

tert-butyl chloride

→

title compound

Rendement 15.0%

2-tert-butyl-4-phenyl-cyclohexanone

Rendement 15.0%

Solvants

dichloromethane

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added
2. 2
   Lavagewashed with ice water
3. 3
   SéchageThe organic phase is dried over sodium sulphate
4. 4
   Autrethe solvent is removed in a vacuum

Mode opératoire

Trimethyl-(4-phenyl-cyclohex-1-enyloxy)-silane (7.27 mmol) and tert-butyl chloride (7.85 mmol) are introduced first in dichloromethane under nitrogen and cooled to −45° C. A solution, also cooled to −45° C., of titanium tetrachloride (7.63 mmol) in dichloromethane (3.6 ml) is added, and stirring is continued for 3 hours at this temperature. The reaction mixture is diluted with dichloromethane and washed with ice water. The organic phase is dried over sodium sulphate and the solvent is removed in a vacuum. Column chromatography (ethyl acetate/heptane 1:4) of the residue produces the title compound (250 mg) in a yield of 15% (Angew Chem Int Ed Engl 1978, 17, 1, 48-49). 1H NMR (ppm, CDCl3): 7.35 (5H); 3.15 (1H); 2.55 (1H); 2.4 (3H); 2.25 (1H); 2 (1H); 1.8 (1H); 1.05 (9H).

Source