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

HRID 1110174

Reaktionsgleichung

Reaktionsgleichung von HRID 1110174
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

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 10% 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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-44f3e5b21991411fa403ac7f1b688cf9
Quelldatensatz
uspto-grants-1994_06
Patentnummer
US05324869

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