HCID 14383745, compound → 4-(2-Propenyl)-2-cyclohexen-1-one

HRID 2406501Notes

Reaction equation

HRID 2406501 reaction equation
C([O:3][C:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH:11]=[CH2:12])[C:6](=O)[CH:5]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH2:10]([CH:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH:5]=[CH:6]1)[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 14383745HCID 14383745, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 109535714-(2-Propenyl)-2-cyclohexen-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (+)-3-ethoxy-6-(2-propenyl)-2-cyclohexen-1-one (300 mg, 1.7 mmol) in dry ether was added to a solution of LAH (30 mg, 0.8 mmol) in dry ether at 0° C. and the mixture was stirred for 1 hour. The reaction was quenched with 2M HCl and stirred for 30 minutes and then extracted with ether. The ethereal extracts were washed with saturated NaHCO3, dried over anhydrous MgSO4 and the solvent was removed under vacuum. The yellow liquid obtained was purified using 20% ethyl acetate/hexane mixture to get the final product as a pale yellow liquid (0.15 g, 65%). Rf (20% ethyl acetate/hexane) 0.56. 1H NMR (300 MHz, CDCl3): ∂ 1.68-1.78 (m, 1H), 2.10-2.18 (m, 1H), 2.2-2.3 (m, 2H), 2.34-2.42 (m, 1H), 2.48-2.56 (m, 2H), 5.1 (d, J=12.5 Hz, 2H), 5.76-5.86 (m, 1H), 6.0 (dd, J=2.4, 10.2 Hz, 1H), 6.9 (d, J=10.2 Hz, 1H). (ESI, Pos) m/z 159.

Workup

  1. customThe reaction was quenched with 2M HCl
  2. stirringstirred for 30 minutes
  3. extractionextracted with ether
  4. washThe ethereal extracts were washed with saturated NaHCO3
  5. dry with materialdried over anhydrous MgSO4
  6. customthe solvent was removed under vacuum
  7. customThe yellow liquid obtained
  8. customwas purified

Sources & evidence

ORD record
ord-0ede1fda30b748d2817e64105d466528
Source dataset
uspto-grants-2014_08
Patent number
US08809373B2

Reaction notes

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