Reaktion #1161673

Reaktionsgleichung

dibromomethane

3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcyclohexanone

lithium dicyclohexylamide

→

3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol

Lösungsmittel

water

tetrahydrofuran

tetrahydrofuran

water

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe ether extract
2. 2
   Trocknenis dried over magnesium sulfate
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe crude product is purified via column chromatography on 500 g of silica gel
5. 5
   Wascheneluted with ether-pentane

Vorschrift

To a -78° C. solution of 17.4 g (0.10 mole) of dibromomethane and 21.7 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcyclohexanone in 100 ml of tetrahydrofuran is added dropwise over a period of 2 hours a solution of lithium dicyclohexylamide (0.10 mole) in 100 ml of tetrahydrofuran. The reaction is stirred one hour longer at -78° C. and quenched by addition of 2 ml (0.11 mole) of water. The reaction is added to 300 ml ether and 200 ml water. The ether extract is dried over magnesium sulfate and evaporated. The crude product is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to give pure 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol.

Quelle