Dimethylformamide → 4-(2-Methylbutan-2-yl)benzaldehyde

HRID 19773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19773
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:21]=[O:22])C>>[CH3:11][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:21]=[O:22])=[CH:3][CH:4]=1)([CH3:12])[CH2:9][CH3:10]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 129009891-Bromo-4-(2-methylbutan-2-yl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 4737804-(2-Methylbutan-2-yl)benzaldehydeAusbeute 90 %

Versuchsvorschrift

The title compound was synthesized in analogy to example S1-A using 1-bromo-4-(1,1-dimethylpropyl)-benzene (synthesized in analogy to a procedure described in J. Chem. Res. Miniprint., 1997, 12, 2701-2733) (250 mg, 1.10 mmol), nBuLi (825 μl, 1.6M solution in hexane, 1.32 mmol) and DMF (427 μl, 5.50 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-(1,1-dimethylpropyl)-benzaldehyde (175 mg, 90%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 9.99 (s, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.50 (d, J=8.5 Hz, 2H), 1.69 (q, J=7.5 Hz, 2H), 1.32 (s, 6H), 0.68 (t, J=7.5 Hz, 3H).

Aufarbeitung

  1. customsynthesized in analogy to a procedure
  2. customThe isolated residue was purified by flash column chromatography (1:9 ether:pentane)

Quellen und Nachweise

ORD-Eintrag
ord-c110833773804ffe919fd0ad2a44a134
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

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