Water → 3-Hydroxy-3-methyl-1-decene

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BK1114. Trimethylsulfonium iodide (23.53 g, 115.3 mmol) was suspended in anhydrous THF (250 mL) under argon and the slurry cooled to −20° C. A pre-cooled (−20° C.) solution of n-BuLi (2.14M in hexanes, 51.2 mL, 109 mmol) was added slowly via cannulating needle and the solution stirred for 10 minutes at −20° C. A pre-cooled (−20° C.) solution 2-nonanone (5.0 mL, 28.8 mmol) was then added slowly via cannulating needle and the resultant solution was stirred at −20° C. for 1 hour. The reaction was allowed to warm to room temperature over 2 hours. Water (200 mL) was added and the mixture was extracted with Et2O (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford an oily residue. This material was chromatographed on silica gel (eluting with 10% EtOAc/hexanes) to afford 3-hydroxy-3-methyl-1-decene (3.56 g, 72% yield) as a colorless oil.

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