Methyl iodide → HCID 14302185, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (8.9 ml, 63.3 mmol) in 100 ml of anhydrous THF was added dropwise n-butyl lithium (1.59N, 39.8 ml, 63.3 mmol) at -78° C. under argon atmosphere. After the mixture was stirred at -78° C. for 30 minutes, methyl 3-cyclohexyl-2-methylpropionate (7.7829 g, 42.2 mmol) was added dropwise. After the mixture was stirred at -78° C. for 30 minutes, a solution of methyl iodide (3.9 ml, 63.3 mmol) in HMPA (2.2 ml, 12.7 mmol) was added dropwise. After being stirred at -78° C. for 1 hour, the reaction mixture was diluted with an aqueous saturated solution of ammonium chloride. The aqueous mixture was extracted with ether (50 ml×4). Then, the combined ether layers were washed water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, and concentrated. The residue was distilled to give a colorless liquid of methyl 3-cyclohexyl-2,2-dimethylpropionate (5.7294 g, yield 52.2%, b.p. 121.5°-123° C./22 mmHg), which was assigned the structure by the following data:

Provenance & Evidence