sodium hydroxide in ethanol T=20°C; 3 h;

1.1: thionyl chloride / 4 h / 60 °C 2.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -40 °C 2.2: CuCN; LiCl / tetrahydrofuran / 0.25 h 2.3: 77 percent / tetrahydrofuran / 1 h 3.1: 81 percent / aq. NaOH / ethanol / 3 h / 20 °C View Scheme

1.1: isopropylmagnesium chloride / tetrahydrofuran / 1 h / -40 °C 1.2: CuCN; LiCl / tetrahydrofuran / 0.25 h 1.3: 77 percent / tetrahydrofuran / 1 h 2.1: 81 percent / aq. NaOH / ethanol / 3 h / 20 °C View Scheme

Yield given. Multistep reaction;

1: 1) Mg / 1) THF, 80 deg C, 2 h, 2) reflux, 15 h 2: 1) Mg, ethyliodine / 1) THF, a) reflux, 3 h, b) stirred overnight, 2) THF, 5-15 deg C, 30 min View Scheme

magnesium; ethyl iodide 1) THF, a) reflux, 3 h, b) stirred overnight, 2) THF, 5-15 deg C, 30 min; Multistep reaction;

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