Diisopropylamine → 1-Cyclohexyl-1-phenyl-1-trimethylsilyloxy-2-propanone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 35 ml (0.25 mole) of diisopropylamine in 800 ml of THF at -78° C. was added 100 ml of a 2.5M solution of n-BuLi in hexane. After the mixture was stirred at -78° C. for 1 hour, 52 g (0.205 mole) of 1-(diethoxyphosphinyl)-1-trimethylsilyloxyethane [prepared according to the procedure of G. H. Birum and G. A. Richardson, U.S. Pat. No. 3,113,139 (1963)] was added dropwise. The mixture was stirred for 1.5 hours at -78° C. and then 42.5 g (0.225 mole) of cyclohexyl phenyl ketone in 100 ml of THF was added dropwise at -78° C. The stirred solution was warmed to room temperature during 30 minutes and then it was poured into 2 L of water. Extraction of the mixture with ether, after washing with dilute hydrochloric acid, drying and concentrating gave 51 g (75%) of colorless liquid.

Provenance & Evidence