potassium carbonate in methanol 2 h; Ambient temperature;

sodium tetrahydroborate in ethanol T=0°C; 0.166667 h; Yield given;

1: 37 percent / SeO2, t-BuOOH / CH2Cl2 / 2 h / Ambient temperature 2: 100 percent / Ph3P, I2, imidazole / diethyl ether; acetonitrile / 0.5 h / Ambient temperature 3: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 4: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 5: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 100 percent / DMAP / pyridine / 0.5 h / Ambient temperature 2: 37 percent / SeO2, t-BuOOH / CH2Cl2 / 2 h / Ambient temperature 3: 100 percent / Ph3P, I2, imidazole / diethyl ether; acetonitrile / 0.5 h / Ambient temperature 4: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 5: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 6: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 18-crown-6, KCN / CH2Cl2 / 0.5 h / 0 °C 2: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 3: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 4: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 2: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 3: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 100 percent / Ph3P, I2, imidazole / diethyl ether; acetonitrile / 0.5 h / Ambient temperature 2: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 3: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 4: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 2: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 3: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 70 percent / MnO2, SiO2 / hexane / 20 h / Ambient temperature 2: 18-crown-6, KCN / CH2Cl2 / 0.5 h / 0 °C 3: 39 percent / LiN(SiMe3)2 / tetrahydrofuran / -78 °C / 1.) 40 min, 2.) 2 h 4: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 5: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme

1: 50 percent / n-Bu4NF / H2O; tetrahydrofuran / 15 h / Ambient temperature 2: 100 percent / K2CO3 / methanol / 2 h / Ambient temperature View Scheme