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Reaction of 2-methyloxetane with allyltrimethylsilane as above gave 3-methyl-5-hexen-l-ol in 20% yield.33 Preparative Reaction of (2-Methylallyl)trimethylsilane with Oxetane. A stirred solution of (2-methylallyl)trimethylsilane, 9.3 g (0.073 mol), and 9.5 mL of oxetane in 25 mL of CH2C12 which was cooled to -100 °C under an atmosphere of nitrogen was prepared. To this was added over about 15 min 8.5 mL of titanium tetrachloride (0.073 mol) dissolved in 15 mL of CH2C12. The reaction was then stirred overnight while it gradually warmed to room temperature. The resulting mixture was then slowly poured into cold 0.1 N potassium hydroxide. The resulting suspension was extracted 3 times with about 60 mL of CH2C12.The organic solution was dried over anhydrous magnesium sulfate and filtered and the solvent removed by evaporation under reduced pressure. The product mixture was filtered through a short column of alumina. A 1:1 mixture of ether/petroleum ether was used as the eluent. This process serves to remove any titanium residues. Failure to follow this procedure may result in isomerization of the carbon-carbon double bond of the product. The volatile material was distilled through a 66-cm vacuum-jacketed column which was packed with a spiral glass band. 3-Chloropropanol distilled at 60-62 °C (25 mm). The desired product 5-methyl-5-hexen-l-ol distilled at 53-54 °C (9 mm), lit. bp 74-76 °C (15 mm).34 Its spectra were in complete agreement with those previously reported. A yield of 5.4 g (0.048 mol), 69% , was obtained.

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