Methyl iodide → HCID 59518507, compound

Participants

Reaction Conditions

Reaction Steps

Compounds of formula (V) can be prepared according to a first representative procedure, as follows: 4,4-dimethylcyclohexane-1,3-dione 7 (1 mole eq) (commercially available) is dissolved in anhydrous diethylether and hexamethylphosphoramide (solvent ratio, 20:1 respectively) under an atmosphere of nitrogen. The mixture is cooled to 0° C. and lithium diisopropylamide (2.1 mole eq) is added dropwise over 40 mins. The mixture is then stirred for a further 10 mins before the addition of methyl iodide (1 mole eq). The mixture is stirred for 12 h and then benzoyl cyanide (2 mole eq) is added and the mixture stirred for a further 24 h. The reaction was quenched with water and the ether layer partitioned and dried (Na2SO4). The solvent was removed and the residue subjected to SiO2 column chromatography (hexane/ethyl acetate) affording 1-benzoyl-3,3,5-trimethylcyclohexan-2,6-dione 8 (Scheme 4).

Provenance & Evidence