(1-Isopropyl-2-methyl-propyl)-(2,4,5-trimethoxy-benzylidene)-amine → (2-Isopropyl4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine

HRID 38327

Reaktionsgleichung

[CH:1]([CH:4]([N:8]=[CH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=1OC)[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH:22]([Li])([CH3:24])[CH3:23]>C1COCC1>[CH:22]([C:11]1[CH:12]=[C:13]([O:18][CH3:19])[C:14]([O:16][CH3:17])=[CH:15][C:10]=1[CH:9]=[N:8][CH:4]([CH:1]([CH3:2])[CH3:3])[CH:5]([CH3:6])[CH3:7])([CH3:24])[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of (1-isopropyl-2-methyl-propyl)-(2,4,5-trimethoxy-benzylidene)-amine (1.024 g, 3.5 mmol) in 35 ml THF at −78° C. was added isopropyllithium (6.0 mL, 0.7 M in pentane) drop-wise over 5 minutes. The solution was allowed to stir 30 min at −78° C. After warming to room temperature over 45 minutes the mixture was quenched by the addition of 5 mL of 10% NH4Cl and concentrated in vacuo. 100 mL of H2O was added and the mixture was extracted with ethyl acetate, washed with H2O and then brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give (2-isopropyl-4,5-dimethoxy-benzylidene)-(1-isopropyl-2-methyl-propyl)-amine as a yellow oil.

Aufarbeitung

temperatureAfter warming to room temperature over 45 minutes the mixture
customwas quenched by the addition of 5 mL of 10% NH4Cl
concentrationconcentrated in vacuo
addition100 mL of H2O was added
extractionthe mixture was extracted with ethyl acetate
washwashed with H2O
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-20f3177712f64e019f91495e5d339632
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524725B2

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