Tetrahydrofuran → 4-Phenyl-2-butanol

Participants

Reaction Conditions

Reaction Steps

A dry Schlenk tube under argon was charged with 48 mg (0.15 mmol) of neodymium (III) isopropoxide. Triethoxysilane (1.4 mL, 7.5 mmol) was added, and the reaction mixture was heated to 60° C. After 0.5 hours, 4-phenyl-2-butanone (450 μL, 3 mmol) was added. After 24 hours, the reaction was complete, as determined by GLC analysis of a aliquot taken from the reaction mixture. THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 12 hours. The mixture was added to water and ether (50 mL of each), shaken vigorously, and separated. The aqueous layer was then extracted with an additional 50 mL of ether, and the combined organic layers were dried over MgSO4. After removal of the drying agent by filtration and concentration of the solution by rotary evaporation, the crude material was purified by flash chromatography (ether:hexane=3:7) to afford 245 mg (54% yield) of 4-phenyl-2-butanol (>95% pure by 1H-NMR analysis).

Provenance & Evidence