TMS-Imidazole → (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one

Beteiligte Stoffe

Reaktionsschritte

323 mg of (4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-octahydro-naphthalen-1-one, was reacted at 40° with 1.33 ml of TMS-imidazole (9 equivalents) in 8 ml of CH2Cl2. After a few hours the mixture was poured onto crushed ice, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=9/1) yielded 326 mg of (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one as colourless oil.

Herkunft & Nachweise