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  (Chem Dev)

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(RMgX + Lactone)


Example 1

To a solution of the SM (5.85 g, 29.1 mmol) in THF (50 mL) at 0 C was added dropwise MeMgBr (3.0 M in ether, 22.4 mL, 67.2 mmol) over 10 min. The reaction mixture was stirred at 0 C for 4 h, then was allowed to warm to RT and stir an additional 15 h. The reaction was quenched with sat aq NH4Cl and extracted with EtOAc (2 x 50 mL). The combined organics were washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (90% EtOAc/hexane) to provide the product as a colorless gum. [6.09 g, 90%]