Dimethylformamide → p-Cyclopentylbenzaldehyde

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 720 mg of a mixture of 1-bromo-4-cyclopentyl-benzene and 1-bromo-4-cyclopent-1-enyl-benzene (˜3.2 mmol), 2.2 ml of a 1.6 molar solution of n-BuLi in hexane (3.52 mmol) and 492 μl of DMF (6.40 mmol). 4-Cyclopentyl-benzaldehyde was isolated by flash column chromatography (5:95 EtOAc/c-hexane) as a yellow liquid (165 mg, 30%). 1H NMR (CDCl3, 300 MHz): δ 1.53-1.91 (m, 6H), 2.11 (m, 2H), 3.07 (quint, J=8.5 Hz, 1H), 7.40 (d, J=8 Hz, 2H), 7.80 (d, J=8 Hz, 2H), 9.97 (s, 1H).

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