6-(m-Methoxyphenyl)hept-1-en-3-one → 2-Ethylcyclopentane-1,3-dione

HRID 1414956Notes

Reaction equation

HRID 1414956 reaction equation
COC1C=[C:5]([CH:9](C)[CH2:10][CH2:11][C:12](=[O:15])C=C)[CH:6]=[CH:7]C=1.C(N(CC)CCC(=O)CCC(C1C=CC=C([O:33]C)C=1)C)C>[OH-].[K+]>[CH2:6]([CH:5]1[C:9](=[O:33])[CH2:10][CH2:11][C:12]1=[O:15])[CH3:7]

Participants

4

Reactant 2

HCID 214856116-(m-Methoxyphenyl)hept-1-en-3-oneHCID 214857581-Diethylamino-6-(m-methoxyphenyl)heptan-3-one

Product 1

HCID 699782-Ethylcyclopentane-1,3-dione

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Reflux a mixture of 6-(m-methoxyphenyl)hept-1-en-3-one and 1-diethylamino-6-(m-methoxyphenyl)heptan-3-one (10 g, obtained by slow distillation of the latter substance) with 2-ethylcyclopentane-1,3-dione (7 g) in 0.12% methanolic potassium hydroxide solution (40 cc) for 15 hours. Remove most of the methanol under reduced pressure and add a mixture of equal volumes of ether and benzene (50 cc). Wash the solution with 5% aqueous sodium hydroxide, water, 10% hydrochloric acid, and brine, and dry. Evaporate the solvent to leave as residue the triketone adduct 2-(6-m-methoxyphenyl-3-oxoheptyl)-2-ethylcyclopentane-1,3-dione (14 g); infrared absorption peak at 5.80 μ.

Workup

  1. temperatureReflux

Sources & evidence

ORD record
ord-400a1fd1811b4360a912469d40442893
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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