Dimethylformamide → 1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

HRID 1268904Notizen

Reaktionsgleichung

[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[Li]CCCC.CN([CH:22]=[O:23])C>C1COCC1>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:22]=[O:23])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

To a solution of the product of Step 1 (112 g, 0.46 mol) in THF (1500 ml) at −60° C. under argon, was added n-BuLi (325 ml, 0.52 mol) over 1 hour. After stirring at −60° C. for 1 hour a solution of DMF (39.7 ml) in THF (50 ml) was added dropwise over 1 hour. The reaction was stirred at −60° C. for 1 hour before being allowed to warm to room temperature. After 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate. The organic phase was then dried (Na2SO4), concentrated in vacuo and the residue purified by silica gel chromatography, to give the title compound (57 g, 65%) as a yellow solid; 1H NMR (CDCl3) 10.0 (1H, s), 7.83–7.73 (3H, m), 4.02 (3H, s), 3.10 (2H, m), 2.92 (2H, m).

Aufarbeitung

additionwas added dropwise over 1 hour
temperatureto warm to room temperature
customAfter 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution
extractionextracted into ethyl acetate
dry with materialThe organic phase was then dried (Na2SO4)
concentrationconcentrated in vacuo
customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-cd987730a5dd4ba183df1092dbed388f
Quelldatensatz: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07199137B2

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