Diethyl Ether → HCID 10443626, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled and stirred ether (700 ml) solution of the (E)-5-methyl-4-tetradecenenitrile (4) (30.0 g, 136 mmols), an n-hexane solution of DIBAL-H (1.7 M, 123 ml, 209 mmols) was added dropwise at −60° C. under an argon gas. The mixture was stirred for 1 hour at −60° C. and for 3 hours at room temperature. The excess reagent was quenched with the addition of HCO2Et (5 ml). After 30 minutes of stirring, the mixture was poured into a saturated aqueous solution of NH4Cl (1.5 L). The resulting mixture was stirred for 20 minutes, acidified with a 20% aqueous solution (1 L) of H2SO4, and extracted with ether. The ether solution was washed with water, dried (MgSO4), and concentrated in a vacuum. The oily residue was subjected to chromatography on Florisil (450 g), and eluted with n-hexane-ether (50:1) to obtain 29.0 g (95.4%) of (E)-5-methyl-4-tetradecenal (5).

Provenance & Evidence