1: With sodium cyanoborohydride; acetic acid in water; acetonitrile T=0 - 20°C; 2: With sodium hydroxide in water; acetonitrile pH=4;

in water T=50°C; 18 h;

tetrabutyl ammonium fluoride in tetrahydrofuran T=25°C; 2 h;

1: H2O / 60 h / 50 °C 2: 3.37 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C View Scheme

1.1: (i-Pr)2NH; BuLi / tetrahydrofuran; hexane / 0.75 h / -100 °C 1.2: 83 percent / Cl2CFCClF2 / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: BuLi / diethyl ether; hexane / 0.75 h / -75 °C 2.2: 89 percent / diethyl ether; hexane 3.1: H2O / 60 h / 50 °C 4.1: 3.37 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C View Scheme

1.1: BuLi / diethyl ether; hexane / 0.75 h / -75 °C 1.2: 89 percent / diethyl ether; hexane 2.1: H2O / 60 h / 50 °C 3.1: 3.37 g / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 25 °C View Scheme