Reaktionsgleichung
[CH:1]1([C:4]2[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Br[C:13]1C=CC(C2(CC)CC2)=C[CH:14]=1.[Li]CCCC.CN(C=O)C>>[CH2:13]([C:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH:8]=[O:9])=[CH:10][CH:11]=2)[CH2:2][CH2:3]1)[CH3:14]Komponenten
5
Versuchsvorschrift
The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 1-bromo-4-(1-ethylcyclopropyl)-benzene (208 mg, 0.92 mmol), n-BuLi (635 μl, 1.6M solution in hexane, 1.02 mmol) and DMF (144 μl, 1.85 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-(1-ethylcyclopropyl)-benzaldehyde (130 mg, 81%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 9.97 (s, 1H), 7.80 (d, J=8.5 Hz, 2H), 7.43 (d, J=8.5 Hz, 2H), 1.65 (q, J=7.5 Hz, 2H), 0.86 (t, J=7.5 Hz, 3H), 0.89-0.82 (m, 2H), 0.79-0.75 (m, 2H).
Aufarbeitung
- customThe isolated residue was purified by flash column chromatography (1:9 ether:pentane)
Quellen und Nachweise
- ORD-Eintrag
- ord-67a05e025ba740358f0fc3bacc62711d
- Quelldatensatz
- uspto-grants-2007_08
- Patentnummer
- US07259183B2
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