Reaktion #48044

Reaktionsgleichung

n-BuLi

DMF

4-cyclopropyl benzaldehyde

1-bromo-4-cyclobutyl-benzene

hexane

→

4-cyclobutyl-benzaldehyde

Ausbeute 67.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe isolated residue was purified by flash column chromatography (5:95 EtOAc/cyclohexane)

Vorschrift

The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S1-A) using 830 mg of 1-bromo-4-cyclobutyl-benzene (3.93 mmol), 2.7 ml of a 1.6 molar solution of n-BuLi in hexane (4.32 mmol) and 605 μl of DMF (7.86 mmol). The isolated residue was purified by flash column chromatography (5:95 EtOAc/cyclohexane) to give 422 mg of 4-cyclobutyl-benzaldehyde (67%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.89 (m, 1H), 1.97-2.26 (m, 3H), 2.40 (m, 2H), 3.63 (quint, J=8.5 Hz, 1H), 7.36 (d, J=8.0 Hz, 2H), 7.81 (d, J=8.0 Hz, 2H), 9.97 (s, 1H).

Quelle