Methyl iodide → HCID 59389287, compound

Participants

Reaction Steps

The compound of Example 180 (830 mg) was dissolved in N,N-dimethylformamide (50 mL) in a stream of argon gas and 60% sodium hydride (135 mg) was added while the solution was stirred in an ice bath. The resulting mixture was stirred at room temperature for 15 min, followed by chilling in an ice bath and addition of methyl iodide (210 μL). The mixture was then stirred at room temperature for 3 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (×2) and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=3:1) afforded the title compound as a pale yellow oil (700 mg).

Provenance & Evidence