tetrabutyl ammonium fluoride in tetrahydrofuran

sodium tris(acetoxy)borohydride in acetic acid; acetonitrile T=0°C; 0.166667 h; Yield given;

1: AsPh3, tri-n-butylamine / Pd(OAc)2 / dimethylformamide / 15 h / 60 °C 2: <n-Bu4N>F / acetic acid; tetrahydrofuran / 0.17 h / 0 °C 3: Na<HB(OAc)3> / acetic acid; acetonitrile / 0.17 h / 0 °C View Scheme

1: 87.7 percent / dimethylformamide / 4 h 2: 9.8 percent / 2,2'-azobis(2-methylpropionitrile), n-Bu3SnH / toluene / 1 h / Heating 3: 89 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: 9.8 percent / 2,2'-azobis(2-methylpropionitrile), n-Bu3SnH / toluene / 1 h / Heating 2: 89 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: 93 percent / pyridine / 4 h / Ambient temperature 2: 87.7 percent / dimethylformamide / 4 h 3: 9.8 percent / 2,2'-azobis(2-methylpropionitrile), n-Bu3SnH / toluene / 1 h / Heating 4: 89 percent / n-Bu4NF / tetrahydrofuran View Scheme

1: <n-Bu4N>F / acetic acid; tetrahydrofuran / 0.17 h / 0 °C 2: Na<HB(OAc)3> / acetic acid; acetonitrile / 0.17 h / 0 °C View Scheme

1.1: HCl / dioxane / 0.42 h / 20 °C 2.1: 15.0 g / imidazole / tetrahydrofuran / 1.5 h / 20 °C 3.1: 4.20 g / aq. CF3COOH / CH2Cl2 / 0.33 h / -15 °C 4.1: 85 percent / pyridinium chloroformate / CH2Cl2 / 16 h / 20 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -100 °C 5.2: tetrahydrofuran; hexane / 3 h / -100 - -78 °C 6.1: 5.20 g / L-Selectride / tetrahydrofuran / -78 - 0 °C 7.1: 3.72 g / diisopropyl azodicarboxylate; Ph3P / tetrahydrofuran / 3 h / 20 °C 8.1: Et4NF / acetonitrile / 1 h / 20 °C 9.1: 0.94 g / CF3COOH / CH2Cl2 / 0.25 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -100 °C 1.2: tetrahydrofuran; hexane / 3 h / -100 - -78 °C 2.1: 5.20 g / L-Selectride / tetrahydrofuran / -78 - 0 °C 3.1: 3.72 g / diisopropyl azodicarboxylate; Ph3P / tetrahydrofuran / 3 h / 20 °C 4.1: Et4NF / acetonitrile / 1 h / 20 °C 5.1: 0.94 g / CF3COOH / CH2Cl2 / 0.25 h / 20 °C View Scheme

1: Et4NF / acetonitrile / 1 h / 20 °C 2: 0.94 g / CF3COOH / CH2Cl2 / 0.25 h / 20 °C View Scheme