Tetrahydrofuran → 2-Octanol

Participants

Reaction Conditions

Reaction Steps

A dry Schlenk tube under argon was charged with triethoxysilane (1.4 ml, 7.5 mmol) and 2-octanone (525 μL, 5 mmol) and heated to 60° C. Titanium (IV) isopropoxide (75 μL, 0.25 mmol) was then added. After stirring at that temperature for an hour the color changed to deep blue. After 12 hours the reaction mixture was cooled to room temperature and added to THF (5 mL). Aqueous NaOH (1 N, 15 mL) was then added to the solution. After vigorous stirring at room temperature for 1 hour, the reaction mixture was added to a water/ether mixture (100 mL each), shaken vigorously, and separated. The aqueous layer was washed with an additional 100 mL of ether, and the combined ether extracts were dried over MgSO4. Concentration in vacuo afforded 401 mg (63% yield, greater than 95% pure by NMR and GC) of 2-octanol as an oil.

Provenance & Evidence