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Grignard

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Examples:

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Example 1

To the SM (480 mg, 2.8 mmol) in dry ether at 0 C was added dropwise a solution of MeMgBr (3M in ether, 2.8 mL, 8.4 mmol). The mixture was slowly allowed to warm to RT and stirred for 3 h. The reaction was quenched with saturated NH4Cl (2 x 20 mL) and extracted with Et2O. The org layer was dried (Na2SO4) and concentrated to provide the product. [200 mg] [WO2010038081, page 135]

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Example 2

To a solution of the SM (1.41 g, 5.31 mmol) in dry THF (27 mL) at 0 C under N2 was added Fe(acac)3 (197 mg, 0.547 mmol), followed by the dropwise addition of N-butylmagnesium chloride (2 M in THF, 12.4 mL, 24.8 mmol). After completion of the addition, the mixture was stirred at 70 C for 5 h, after which time it was cooled to RT and quenched with H2O (10 mL). The THF was removed in vacuo and the resulting mixture was extracted with DCM (50 mL). The org layer was separated, washed with brine (10 mL), dried (Na2SO4), concentrated, and purified by silica gel chromatography (0-5% EtOAc/DCM) to provide the product as an orange oil. [867 mg, 57%] [WO2012112946, page 207]