Water → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

HRID 1464468Notes

Reaction equation

HRID 1464468 reaction equation
[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[C:5]#N)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.O.C(O)(=O)C(O)=[O:35]>CCCCCC.C1(C)C=CC=CC=1>[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH:5]=[O:35])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 21225700DiisobutylaluminumhydrideHCID 536571452-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

Product 1

HCID 544419182-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenalYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

To a solution of 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (856 mg, 3.0 mmol) in n-hexane.(30 ml) was added a 0.5M solution of diisobutylaluminium hydride in toluene (6 ml) with stirring at -70° C. under argon atmosphere. After one hour, water (3 ml) was added, the cooling bath was removed, and the reaction mixture was stirred well. Resultant white precipitates were filtered and washed. The filtrate was concentrated to give a residue, which was dissolved in n-hexane (10 ml). The n-hexane solution was combined with a aqueous solution of oxalic acid (5 ml) and stirred for 3 hours. The organic layer was extracted and separated, washed with water, dried over MgSO4, and concentrated. The resultant residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=10:1) to obtain 2 -(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (865 mg, 84%).

Workup

  1. customthe cooling bath was removed
  2. stirringthe reaction mixture was stirred well
  3. customResultant white precipitates
  4. filtrationwere filtered
  5. washwashed
  6. concentrationThe filtrate was concentrated
  7. customto give a residue, which
  8. stirringstirred for 3 hours
  9. extractionThe organic layer was extracted
  10. customseparated
  11. washwashed with water
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-14cfc73297564c54b66f72225a723123
Source dataset
uspto-grants-1994_04
Patent number
US05304661

Reaction notes

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