Dimethylformamide → 2,4-Bis-methoxymethoxy-6-methoxymethyl-benzaldehyde

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Reaktionsgleichung

Br[C:2]1[C:7]([CH2:8][O:9][CH3:10])=[CH:6][C:5]([O:11][CH2:12][O:13][CH3:14])=[CH:4][C:3]=1[O:15][CH2:16][O:17][CH3:18].[Li]CCCC.CN([CH:27]=[O:28])C>CCOCC>[CH3:18][O:17][CH2:16][O:15][C:3]1[CH:4]=[C:5]([O:11][CH2:12][O:13][CH3:14])[CH:6]=[C:7]([CH2:8][O:9][CH3:10])[C:2]=1[CH:27]=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 17.59 mmol) in Et2O (60 mL) was added n-BuLi (15.47 mL, 2.5 M in Hexane) at −78° C. After stirring for 1 hour at −78° C., DMF (13.6 mL, 175.8 mmol) was the added and reaction mixture was allowed to warm to room temperature over 3 hours. The reaction was quenched with saturated NH4Cl and extracted with Et2O. The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (3.93 g, 82%). 1H NMR (400 MHz, CDCl3δ 10.50 (s, 1H), 7.03 (s, 1H), 6.77 (s, 1H), 5.30 (s, 2H), 5.27 (s, 2H), 4.80 (s, 3H), 3.50 (s, 3H), 4.49 (s, 3H).

Aufarbeitung

additionadded
customreaction mixture
temperatureto warm to room temperature over 3 hours
customThe reaction was quenched with saturated NH4Cl
extractionextracted with Et2O
customThe organic extracts were dried
concentrationconcentrated in vacuo
customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-2ffb4afab5834de892ca0971f1354952
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08343944B2

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