1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h View Scheme

1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h 3: 80 percent / 1,2-dimethoxy-ethane / 4 h / 170 °C 4: 45 percent / n-Butyllithium / tetrahydrofuran View Scheme

1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h 3: 80 percent / 1,2-dimethoxy-ethane / 4 h / 170 °C 4: 45 percent / n-Butyllithium / tetrahydrofuran 5: 0.481 g / chloroamine, aq. sodium hydroxide / diethyl ether / 1.33 h / 10 °C View Scheme

1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h 3: 80 percent / 1,2-dimethoxy-ethane / 4 h / 170 °C 4: 45 percent / n-Butyllithium / tetrahydrofuran 5: 0.481 g / chloroamine, aq. sodium hydroxide / diethyl ether / 1.33 h / 10 °C 6: 0.265 g / NaOCH3 / methanol / -90 - -85 °C / Irradiation View Scheme

1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h 3: 80 percent / 1,2-dimethoxy-ethane / 4 h / 170 °C 4: 45 percent / n-Butyllithium / tetrahydrofuran 5: 0.481 g / chloroamine, aq. sodium hydroxide / diethyl ether / 1.33 h / 10 °C 6: 0.265 g / NaOCH3 / methanol / -90 - -85 °C / Irradiation 7: 96 percent / LiAlH4 / diethyl ether / 1.5 h / Ambient temperature View Scheme

1: diisobutyl-aluminumhydride / hexane; 1,2-dimethoxy-ethane / -78 °C 2: n-Butyllithium / tetrahydrofuran / 5 h 3: 80 percent / 1,2-dimethoxy-ethane / 4 h / 170 °C View Scheme