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

HRID 1637032Notes

Reaction equation

HRID 1637032 reaction equation
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10](=O)[CH:11]=[CH:12][CH:13]=[CH:14][CH3:15].[BH4-].[Na+]>C(O)C>[CH2:10]([NH:9][C@@H:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)/[CH:11]=[CH:12]/[CH:13]=[CH:14]/[CH3:15]

Participants

5

Reactant 3

HCID 8901Hexa-2,4-dienalHCID 758181-Phenethylamine, (-)-HCID 4311764Sodium borohydride

Product 1

HCID 86755222HCID 86755222, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customwas removed under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  4. washThis solution was washed with brine (30 ml)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an orange oil
  9. customThis was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:4)]
  10. distillationfollowed by distillation under reduced pressure [130° C. 1 mmHg]

Sources & evidence

ORD record
ord-0d19535262af4bb9bb031e7302a09ae2
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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