1: With naphthalene; lithium in tetrahydrofuran T=-20°C; 8 h; 2: With water in tetrahydrofuran 0.5 h;

sodium hydrogencarbonate in ethanol Heating;

1.1: 87 percent / p-toluenesulfonic acid / toluene / Heating 2.1: Li; naphthalene / tetrahydrofuran / 3 h / -40 °C 2.2: H2O / tetrahydrofuran / 0.5 h / -40 °C 3.1: Li; naphthalene / tetrahydrofuran / 8 h / -20 °C 3.2: 85 percent / H2O / tetrahydrofuran / 0.5 h View Scheme

1.1: Li; naphthalene / tetrahydrofuran / 3 h / -40 °C 1.2: H2O / tetrahydrofuran / 0.5 h / -40 °C 2.1: Li; naphthalene / tetrahydrofuran / 8 h / -20 °C 2.2: 85 percent / H2O / tetrahydrofuran / 0.5 h View Scheme

sodium tetrahydroborate in ethanol 1 h; Ambient temperature;

in methanol 3 h; Heating;

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