Hexamethylphosphoramide → HCID 86754551, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (-40° C.) solution of 46 mL (21 mmol) of LDA (prepared as mentioned above from 2.9 mL of diisopropylamine and 13 mL of n-BuLi in 30 mL of THF) under argon was added a solution of 1.69 g (10.3 mmol) of (5R,6S)-2,6-dimethyl-5-isopropenyl-2-cyclohexen-1-one in 30 mL of ether was added via cannula, an the resulting solution was stirred at 0° C. for 45 min. To it, 1.8 mL (10 mmol) of HMPA was added, stirred at the same temperature for 4 hours, and a solution of 5.68 g (22 mmol) of (cis-3-iodo-2-propenyl) methanesulfonate (40)2 in 30 mL of ether was added. After stirring at room temperature for 12 hours, the reaction mixture was poured into an aqueous solution of NaHCO3, extracted three times with ether, and the combined extracts were washed with brine, dried (MgSO4), and concentrated. The residue was column chromatographed on silica gel using a hexane:methylene chloride (3:2) as eluant to give 2.48 g (73% yield) of 41 and 0.237 g (14% recovery) of the starting material.

Provenance & Evidence