Dimethylformamide → Methyl 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate

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Reaction Steps

A solution of methyl 3-trifluoromethylsulfonyloxy-5,6,7,8-tetrahydro-1-naphthalenecarboxylate (2.08 g, 6.15 mmol), zinc cyanide (0.81 g, 6.89 mmol) and tetrakistriphenylphosphine palladium (0.56 g, 0.48 mmol) in DMF (8 mL) was stirred at 120° C. for 1 h. The mixture was diluted with saturated NaHCO3, extracted with EtOAc, dried (MgSO4), filtered, and concentrated. Following column chromatography methyl-3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylate was obtained as a white solid (960 mg, 73%). 1H NMR (CDCl3) δ 7.94 (s, 1H), 7.49 (s, 1H), 3.90 (s, 3H), 3.11 (s, 2H), 2.84 (s, 2H), 1.81 (m, 4H); MS m/z 216.1 (M+H), 214.1 (M−H).

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