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

HRID 1077142

Reaction equation

HRID 1077142 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-ethyl-cyclopentane-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-560f679c025c4f268ca1059d16410c92
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Linked notes

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