1-Diethylamino-6-(3,4-dimethoxyphenyl)hexan-3-one → 2-Ethylcyclopentane-1,3-dione

HRID 1414959Notes

Reaction equation

HRID 1414959 reaction equation
COC1C=[C:5]([CH2:11][CH2:12][CH2:13]C(=O)C=C)[CH:6]=[CH:7][C:8]=1[O:9]C.C[O:19]C1C=C(CCCC(=O)CCN(CC)CC)C=CC=1OC>[OH-].[K+]>[CH2:12]([CH:11]1[C:5](=[O:19])[CH2:6][CH2:7][C:8]1=[O:9])[CH3:13]

Participants

4

Reactant 2

HCID 214854151-Diethylamino-6-(3,4-dimethoxyphenyl)hexan-3-oneHCID 214857326-(3,4-Dimethoxyphenyl)hex-1-en-3-one

Product 1

HCID 699782-Ethylcyclopentane-1,3-dione

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Reflux 6-(3,4-dimethoxyphenyl)hex-1-en-3-one, containing a small amount of 6-(3,4-dimethoxyphenyl)-1-diethylaminohexan-3-one (6 g, produced by slow distillation of the latter substance) with 2-ethylcyclopentane-1,3-dione (3.5 g) in 0.12% anhydrous methanolic potassium hydroxide (10 cc) for 10 hours. Remove most of the methanol under reduced pressure, add benzene (25 cc) and ether (25 cc) and wash the solution with water, dilute aqueous potassium hydroxide, dilute hydrochloric acid and water. Dry and evaporate the solvent to give the triketone adduct 2-[6-(3,4-dimethoxyphenyl)-3-oxohexyl]-2-ethylcyclopentane-1,3-dione; infrared absorption (gum) 5.80, 6.25 μ (split peak).

Sources & evidence

ORD record
ord-237a621020b4448eb6466d47d36f2cc4
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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