Ketone, 2,4-dimethylpyrrol-3-yl methyl → HCID 18470692, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-acetyl-2,4-dimethyl-1H-pyrrole (commercially available from Aldrich Chem. Co. Inc., 1.50 g, 10.6 mmol) in DMF (40 mL) was added NaH (60% oil dispersion, 0.85 g, 21.2 mmol) at room temperature under nitrogen. After stirring for 30 minutes at room temprature the resulting suspension was cooled to 0° C. and added 2-(trimethylsilyl)ethoxymethyl chloride (3 mL, 15.9 mmol). The reaction mixture was warm to room temperature and stirred for 3 hours. The mixture was quenched with aqueous saturated NaHCO3 solution, and the whole extracted with diethyl ether (100 mL×2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, concentrated iii vaciio. Chromatographic purification of the crude product eluting ethyl acetate-hexane (1:10) gave the subtitle product (2.32 g, 82% yield).

Provenance & Evidence