Hexa-2,4-dienal → HCID 86755222, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-α-methylbenzylamine (1) (1.00 g, 8.25 mmol) in ethanol (20 ml) was added 2,4-hexadienal (0.833 g, 8.66 mmol) and the resulting mixture was refluxed for 1 hour. The solution was cooled to 0° C. and sodium borohydride (0.468 g, 12.38 mmol) was slowly added in portions. This solution was allowed slowly to warm to room temperature overnight (16 hours) after which the ethanol was removed under reduced pressure and the residue dissolved in ethyl acetate (50 ml). This solution was washed with brine (30 ml), dried (magnesium sulphate), filtered and evaporated to give an orange oil. This was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:4)], followed by distillation under reduced pressure [130° C. 1 mmHg] to afford the title compound (3) as a colourless oil (1.51 g, 91%), δH (300 MHz; CDCl3) 7.37-7.21 (5H, m, Ph), 6.08 (2H, m, CH=CH--CH=CH), 5.63 (2H, m, CH=CH--CH=CH), 3.80 (1H, q, J=6.6, PhCHCH3), 3.10 (2H, d, J=6.5, NCH2), 1.74 (3H, d, J=6.8, CH=CHCH3), 1.49 (1H, br s, NH), 1.36 (3H, d, J=6.8, PhCHCH3).

Provenance & Evidence