Methyl iodide → HCID 69181369, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyllithium (200 mL, 340 mmol, 2.4 equiv, 1.7M in pentane) is added dropwise to a cold (−65° C.) solution of (3,5-dimethoxy-phenyl)-carbamic acid tert-butyl ester (36.1 g, 142 mmol) in THF (250 mL), under an argon atmosphere. The mixture is stirred for min at −65° C. and then allowed to warm to −25° C. A solution of methyliodide (10.7 mL, 171 mmol, 1.2 equiv) in THF (140 mL) is then added. The reaction mixture is allowed to stir for 1 h at −25° C. and then poured onto a mixture of ice/H2O (300 mL) and EtOAc (300 mL). The layers are separated and the aqueous phase is extracted with EtOAc (2×150 mL). The combined organic phase is washed with H2O (3×150 mL) and brine (200 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (Hex/acetone, 95:5→9:1→4:1) to provide the title compound. ESI-MS: 268.1 [MH]+, TLC: Rf=0.25 (Hex/acetone, 9:1).

Provenance & Evidence