Diethyl Ether → HCID 89739088, compound

HRID 1468249Notes

Reaction equation

HRID 1468249 reaction equation
[CH:1]1(/[CH:7]=[C:8](\[CH3:14])/[CH2:9][CH:10]([CH3:13])[CH:11]=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>C1CCCCC1.[Pd].ClCCl>[CH:1]1([CH2:7][CH:8]([CH3:14])[CH2:9][CH:10]([CH3:13])[CH:11]=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 517045Sodium AcetateHCID 897389364-​Pentenal, 5-​cyclohexyl-​2,​4-​dimethyl-​, (4E)​-HCID 178418287HCID 178418287, compound

Product 1

HCID 89739088HCID 89739088, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent2×HCID 8078CyclohexaneSolvent

Procedure

(E)-5-cyclohexyl-2,4-dimethylpent-4-enal (2.18 g; 11 mmol) was hydrogenated at 20 bar and room temperature in cyclohexane (20 ml) in the presence of 5% w/w palladium on charcoal (0.18 g). The thus obtained crude product was dissolved in dry dichloromethane (20 ml) and added drop-wise to a mixture of anhydrous sodium acetate (5 g) and finely ground pyridinium chlorochromate (PCC; 4.84 g; 22 mmol) in dry dichloromethane (50 ml) at 0° C. under nitrogen. The reaction was then stirred for 2 hours at room temperature. Diethyl ether (400 ml) was added to the reaction. After stirring for 30 minutes, the reaction was filtered through a short pad of silica gel, rinsing with diethyl ether. The product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 20:1) followed by bulb-to-bulb distillation (60° C./0.1 mbar). The product was obtained with a yield of 51% as a mixture of diastereoisomers.

Workup

  1. customThe thus obtained crude product
  2. additionadded drop-wise
  3. stirringAfter stirring for 30 minutes
  4. filtrationthe reaction was filtered through a short pad of silica gel
  5. washrinsing with diethyl ether
  6. customThe product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 20:1)
  7. distillationfollowed by bulb-to-bulb distillation (60° C./0.1 mbar)
  8. customThe product was obtained with a yield of 51% as a mixture of diastereoisomers

Sources & evidence

ORD record
ord-05fe674b0be049c2afcd229ee58e412c
Source dataset
uspto-grants-2015_04
Patent number
US09000226B2

Reaction notes

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