diisobutylaluminium hydride in tetrahydrofuran; toluene T=-78°C; 2.5 h;

in tetrahydrofuran; water; acetic acid; toluene

1: NaH / tetrahydrofuran / 64 h 2: acetic acid, 48percent HBr / 0.25 h / 100 °C 3: 71 percent / DIBAL-H / tetrahydrofuran; toluene / 2.5 h / -78 °C View Scheme

1: 65 percent / 1 N NaOH / 1 h / Heating 2: NaH / tetrahydrofuran / 64 h 3: acetic acid, 48percent HBr / 0.25 h / 100 °C 4: 71 percent / DIBAL-H / tetrahydrofuran; toluene / 2.5 h / -78 °C View Scheme

1: 75 percent / NaOCl (Clorox) / Ambient temperature 2: 57 percent / tetrahydrofuran / 3 h / Heating 3: 65 percent / 1 N NaOH / 1 h / Heating 4: NaH / tetrahydrofuran / 64 h 5: acetic acid, 48percent HBr / 0.25 h / 100 °C 6: 71 percent / DIBAL-H / tetrahydrofuran; toluene / 2.5 h / -78 °C View Scheme

1: 57 percent / tetrahydrofuran / 3 h / Heating 2: 65 percent / 1 N NaOH / 1 h / Heating 3: NaH / tetrahydrofuran / 64 h 4: acetic acid, 48percent HBr / 0.25 h / 100 °C 5: 71 percent / DIBAL-H / tetrahydrofuran; toluene / 2.5 h / -78 °C View Scheme