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

HRID 855298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855298
C1(C2C=CC([CH:8]=[O:9])=CC=2)CC1.Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH3:23])([CH3:22])[CH2:20][CH3:21])=[CH:15][CH:14]=1.[Li]CCCC.CN(C=O)C>>[CH3:22][C:19]([C:16]1[CH:17]=[CH:18][C:13]([CH:8]=[O:9])=[CH:14][CH:15]=1)([CH3:23])[CH2:20][CH3:21]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 115064744-CyclopropylbenzaldehydeHCID 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 4-cyclopropyl benzaldehyde (described in example S53) using 1-bromo-4-(1,1-dimethylpropyl)-benzene [synthesized in analogy to a procedure described in J. Chem. Res. Miniprint. 12:2701-2733 (1997)] (250 mg, 1.10 mmol), n-BuLi (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): δ 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-93acedd20f2342d093def5acbaf53e5f
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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