Methyl iodide → HCID 59568838, compound

Participants

Reaction Steps

To a suspension of NaH (468 mg of a 60% dispersion in mineral oil, 11.7 mmol) in 35 mL THF was slowly added 3-[1,3]Dioxolan-2-yl-1-o-tolyl-propan-1-ol (290.0 mg, 1.3 mmol) as a solution in 15 mL THF at room temperature followed by the dropwise addition of methyl iodide (624 L, 1.4 g, 9.6 mmol). The mixture was stirred for 3 h at room temperature before being quenched by the careful addition of saturated aqueous NH4Cl (40 mL). The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL) and dried over sodium sulfate. The solvents were evaporated under reduced pressure and the product isolated by flash column chromatography eluting with 0% to 30% ethyl acetate/hexane to give 285 mg of the title compounds as an oil.

Provenance & Evidence