Carbon Dioxide → HCID 19041776, compound

Participants

Reaction Conditions

Reaction Steps

2-(3,4-dimethoxy-5-iodophenyl)-1,3-dioxane (42) (FIG. 22) (1.7 g, 4.86 mmole) was dissolved in 40 ml dry THF and cooled to -78° C. under an argon atmosphere. n-butyllithium (4.3 ml of a 1.25M soln.) was added and the reaction was warmed to 0° C. and was stirred at that temperature for an additional 45 minutes. The aryl lithium solution was then poured onto solid carbon dioxide covered with anhydrous diethyl ether. A white precipitate formed immediately. Water was added and the organic solvent subsequently removed in vacuo. The remaining aqueous solution was extracted with ethyl acetate. The organic layer was washed with 5% sodium thiosulfate, water, and then stirred vigorously over an equivolume of 10% HCl overnight. The organic layer was separated and the product extracted into 10% K2CO3. The basic solution was acidified with 10% HCl and the product extracted into chloroform. The organic layer was dried over MgSO4, and concentrated in vacuo to a white solid (0.412 g, 40%). The solid can be recrystallized from hexane/ethyl acetate.

Provenance & Evidence