Dimethylformamide → 4-(1-Methylcyclopropyl)benzaldehyde

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 1-bromo-4-(1-methylcyclopropyl)-benzene (2.10 g, 9.95 mmol), nBuLi (9.33 ml, 1.6M solution in hexane, 14.92 mmol) and DMF (3.87 ml, 49.74 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 4-(1-methylcyclopropyl)-benzaldehyde (1.28 g, 80%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 9.96 (s, 1H), 7.79 (d, J=8.5 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 1.46 (s, 1H), 0.98-0.93 (m, 2H), 0.90-0.84 (m, 2H).

Provenance & Evidence