in toluene 2 h; Heating;

tetrabutyl ammonium fluoride in tetrahydrofuran T=-78 - 20°C; 0.2 h; Inert atmosphere;

1: thionyl chloride; silver nitrate / tetrahydrofuran / 25 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.2 h / -78 - 20 °C / Inert atmosphere View Scheme

1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2: sodium tetrahydroborate / methanol / 6 h / 20 °C / Inert atmosphere 3: thionyl chloride; silver nitrate / tetrahydrofuran / 25 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.2 h / -78 - 20 °C / Inert atmosphere View Scheme

1: sodium tetrahydroborate / methanol / 6 h / 20 °C / Inert atmosphere 2: thionyl chloride; silver nitrate / tetrahydrofuran / 25 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.2 h / -78 - 20 °C / Inert atmosphere View Scheme

Addition; 1 h;

1: 100 percent / HCl / -10 - 4 °C 2: 45 percent / 1 h View Scheme

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