Isophorone → 3-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]-5,5-dimethyl-2-cyclohexenone

HRID 85292

Reaktionsgleichung

[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.[O-]CC.[Na+].[CH2:15]([N:19]([CH2:30][CH2:31][CH2:32][CH3:33])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:16][CH2:17][CH3:18].C(OCC)(=O)C>O1CCCC1>[CH2:15]([N:19]([CH2:30][CH2:31][CH2:32][CH3:33])[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[CH:10][C:4]2[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2](=[O:1])[CH:3]=2)=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:16][CH2:17][CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

In 15 ml of tetrahydrofuran, 1.5 g (10.85 mmol) of isophorone was dissolved, and 3.4 g of sodium ethoxide (20% solution in ethanol) (10.0 mmol) was added thereto. To this mixture, 2.6 g (9.87 mmol) of 4-dibutylamino-2-methoxybenzaldehyde in tetrahydrofuran was added dropwise with heating at 50° C., and the mixture was stirred for 4.5 hours. To the mixture, 100 ml of ethyl acetate was added. Washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography to give 1.7 g of a reddish orange oily matter (yield: 45.0%).

Aufarbeitung

washWashing with a saturated saline solution
dry with materialdrying over anhydrous sodium sulfate, and concentration
customThe residue was purified by silica gel column chromatography
customto give 1.7 g of a reddish orange oily matter (yield: 45.0%)

Quellen und Nachweise

ORD-Eintrag: ord-19e301df09d24f28bc8d5a9e1c5a6ef8
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846955B2

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