Ethyl Acetate → HCID 22158154, compound

Participants

Reaction Steps

To a suspension of LiAlH4 (1.0 g) in dry THF (25 ml) under dry N2 was added a solution of 2-methyl-2-(3-propyloxyphenyl)propionitrile (1.02 g) in dry THF (10 ml) over 10 minutes. After stirring at 25° for 20 minutes, the reaction mixture was heated under reflux for 5 hours, cooled to 0°, diluted with ether (50 ml) and cautiously decomposed with ethyl acetate (2 ml) followed by 5M NaOH (5 ml). The mixture was filtered and the residue triturated with ether (3×10 ml). The combined filtrates were extracted with 20% HCl (4×10 ml) and the combined extracts basified with 10M NaOH. The liberated oil was extracted into ether (3×15 ml) and the combined extracts dried over Na2SO4, filtered and evaporated to dryness to give a colourless oil.

Provenance & Evidence