Triethoxysilane → 4-Phenyl-2-butanol

Participants

Reaction Conditions

Reaction Steps

A dry Schlenk tube under argon was charged with 37 mg (0.15 mmol) of yttrium (III) isopropoxide (Y5O(iPrO)13). 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. After work-up as in Example 13, the crude material was purified by flash chromatography (ether:hexane=3:7) to afford 235 mg (of 4-phenyl-2-butanol (>93% pure by 1H-NMR analysis, 48% adjusted yield).

Provenance & Evidence