N,N,N',N'-Tetramethylethylenediamine → HCID 58223482, compound

Participants

Reaction Steps

To a tetrahydrofuran (45 ml) solution of 1-cyclopropyl-3,5-dimethoxybenzene (1.59 g, 8.92 mmol) was added N,N,N,N-tetramethylethylenediamine (2.01 ml, 13.4 mmol) at room temperature and 2.77M n-butyllithium (4.83 ml, 13.4 mmol) was added dropwise at −78° C., and the mixture was stirred at room temperature for two hours. The temperature was returned to −78° C. again, trimethyl borate (1.49 ml, 13.4 mmol) was added dropwise and warmed to room temperature, and the mixture was stirred for 13 hours. After the reaction was completed, a saturated aqueous solution of ammonium chloride was added to the reaction mixture while cooling on ice, which was extracted with ethyl acetate and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-heptane/ethyl acetate: 3/1) to obtain the title compound (1.36 g, 6.12 mmol).

Provenance & Evidence