Methyl iodide → HCID 17798127, compound

Participants

Reaction Conditions

Reaction Steps

A solution of sodium hydride(840 mg) in DMSO(200 mL) was stirred at 60-70° C. for 30 min. After addition of THF (60 mL), the mixture was cooled down to 0° C. To the mixture were added dropwise a solution in DMSO of the compound (7g) obtained in Example 36 <step 2>, then methyl iodide (1.33 mL). After stirring for 1 hour, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was suspended in dioxane (5 mL) and to the suspension was added DDQ (1.22 g). The mixture was heated under reflux for 3 hours. After allowing the reaction mixture to cool to room temperature, IN sodium hydroxide (20 mL) and ethyl acetate (50 mL) were added. The precipitated crystals were collected by filtration and washed with water and ethanol. The resultant compound (1.1 g) was suspended in dioxane (60 mL) and to the suspension was added DDQ (1.2 g). The mixture was heated under reflux for 3 hours. After allowing the reaction mixture to cool to room temperature, to the mixture were added 1N-sodium hydroxide (20 mL) and ethyl acetate(50 mL). The precipitated crystals were collected by filtration and washed with water and ethanol to obtain the title compound (1.1 g; 11%).

Provenance & Evidence