Water → HCID 57771552, compound

HRID 2070557Notes

Reaction equation

HRID 2070557 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:20])[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[C:9]1[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O.[OH-].[Na+]>C(OCC)C>[CH3:7][C:8]1([CH3:20])[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]=[C:9]1[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57771573HCID 57771573, compound

Product 1

HCID 57771552HCID 57771552, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (250 mg) in diethyl ether (20 mL) was added dropwise a solution of 4,4-dimethyl-3-pent-4-enyl-cyclohex-2-enone (1.05 g) obtained in Step 2 in diethyl ether (5 mL) under ice-cooling and nitrogen atmosphere, followed by stirring the reaction mixture under ice-cooling for 30 minutes. Then, after successive dropwise addition of water (0.25 mL), 4N aqueous sodium hydroxide solution (0.25 mL) and water (0.75 mL), the reaction mixture was stirred at room temperature for 30 minutes. After the resulting insolubles were filtered off, the filtrate was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=15:1 to 10:1) to give 4,4-dimethyl-3-pent-4-enyl-cyclohex-2-enol (830 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  4. filtrationAfter the resulting insolubles were filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=15:1 to 10:1)

Sources & evidence

ORD record
ord-76e9374c33f44c6f8c34ce9233d1da50
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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