sodium tert-pentoxide in toluene 0.166667 h; Heating; Yields of byproduct given;

1: 87 percent / imidazole / dimethylformamide / 72 h / Ambient temperature 2: diethyl ether / 42 h / Ambient temperature 3: conc. HCl / acetone; H2O / 0.33 h / Ambient temperature 4: 1.) L-Selectride, 2.) pyridine / 1.) THF, -78 to 0 deg C over 1 h, 2.) 40 deg C, 2 h 5: sodium tert-amylate / toluene / 0.17 h / Heating View Scheme

1: 87 percent / imidazole / dimethylformamide / 72 h / Ambient temperature 2: diethyl ether / 42 h / Ambient temperature 3: conc. HCl / acetone; H2O / 0.33 h / Ambient temperature 4: 1.) L-Selectride, 2.) pyridine / 1.) THF, -78 to 0 deg C over 1 h, 2.) 40 deg C, 2 h 5: sodium tert-amylate / toluene / 0.17 h / Heating View Scheme

sodium tert-pentoxide in toluene 0.166667 h; Heating; Yields of byproduct given;

15-crown-5; sodium tert-pentoxide in toluene; benzene 0.166667 h; Heating; Yields of byproduct given;