Hexane → 4-(4-Nitrophenyl)butanal

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To a stirred solution of methyl 4-(4-nitrophenyl)butanoate (63) (0.45 g, 2.02 mmol) in dichloromethane (30 mL), 1M diisobutylaluminum hydride (DIBAL) solution in hexane (2.62 mL, 2.62 mmol) was added at −78° C. After 30 min, the reaction mixture was quenched with saturated Rochelle's salt solution. The resulting mixture was stirred at 21° C. until both phases were clearly separated and the organic layer was clear. After extraction, the separated organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The crude 4-(4-Nitrophenyl)butanal (64) was purified by flash column chromatography (hexane:ethyl acetate, 8:1) to give 4-(4-Nitrophenyl)butanal (64) (0.28 g, 72%): 1H NMR δ 9.79 (s, 1H), 8.16 (d, 2H, J=8.7 Hz) 7.34 (d, 2H, J=8.7 Hz) 2.77 (t, 2H, J=7.7 Hz) 2.51 (t, 2H, J=7.1 Hz), 1.95-2.04 (m, 2H).

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