Methyl iodide → HCID 11276376, compound

Participants

Reaction Conditions

Reaction Steps

At −78° C., 2.7 ml of a 2.5 M solution of n-butyllithium in hexane were added to a solution of 0.95 ml of diisopropylamine (6.75 mmol) in 30 ml of THF, and the mixture was then briefly warmed to −10° C. The mixture was once more cooled to −78° C., 1.24 g (5.63 mmol) of ethyl 4-methoxy-2,3-dihydro-1H-indene-2-carboxylate [Beilstein Reg. No. 8980172], dissolved in 10 ml of THF, were added dropwise, and the solution was stirred for another hour. 0.46 ml (7.32 mmol) of iodomethane was then added dropwise to the reaction solution, and the reaction mixture was stirred at −78° C. for a further 2 hours. After the reaction had gone to completion, saturated aqueous ammonium chloride solution was added quickly to the reaction mixture. After phase separation, the aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried over magnesium sulfate. After filtration, the solvent was removed to dryness under reduced pressure. The crude product obtained was purified by flash chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 1.19 g (5.08 mmol, 90% of theory) of a colorless solid.

Provenance & Evidence