Ethyl caprate → 1-Decanol

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) and ethyl decanoate (696 μL, 3 mmol) were added and the reaction mixture was heated to 60° C. After 7 hours exposure of the reaction mixture to air caused a flame, presumably due to SiH4 gas evolution. After 29 hours, THF (8 mL) and aqueous NaOH (1 N, 15 mL) were added, and the mixture was stirred vigorously for 2.5 hours. The reaction was worked up as in Example 13. Purification by flash chromatography (ether:hexane=3:7) afforded 114 mg (24% yield) of pure decanol and 263 mg (44% yield) of recovered starting material (both >95% pure by 1H-NMR analysis).

Provenance & Evidence