lithium bromide in tetrahydrofuran 18 h; Heating; Yield given;

1: 69 percent / 1,4-diazabicyclo[2.2.2]octane / CH2Cl2 / 96 h / 20 °C 2: LiBr / acetone / 16 h / Heating View Scheme

1: 85 percent / PDC / dimethylformamide / 2 h / 0 °C 2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, hexane, -78 deg C, 1 h then RT 3: MeOH, act. Dowex AG 50W acidic ion exch. resin / 3 h / 40 °C 4: Et3N / CH2Cl2 / 1 h / 0 °C 5: LiBr / tetrahydrofuran / 18 h / Heating View Scheme

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, hexane, -78 deg C, 1 h then RT 2: MeOH, act. Dowex AG 50W acidic ion exch. resin / 3 h / 40 °C 3: Et3N / CH2Cl2 / 1 h / 0 °C 4: LiBr / tetrahydrofuran / 18 h / Heating View Scheme

lithium bromide in acetone 16 h; Heating;

1: 86 percent / LiAlH4 / diethyl ether / 1.25 h / 0 °C 2: 69 percent / 1,4-diazabicyclo[2.2.2]octane / CH2Cl2 / 96 h / 20 °C 3: LiBr / acetone / 16 h / Heating View Scheme

2: 95 percent / sodium bismethoxyethoxyaluminum hydride (Red-Al) / diethyl ether / 1.) 0 deg C, 1 h; 2.) room temp., 12 h 3: 85 percent / pyridinium dichromate / dimethylformamide / 2 h / 0 °C 4: n-BuLi / tetrahydrofuran / 1 h / -78 °C 5: Dowex AG 50 W acidic ion exchange resin / methanol / 3 h / 40 °C 6: Et3N / CH2Cl2 / 1 h / 0 °C 7: LiBr / tetrahydrofuran / 18 h / Heating View Scheme