2: 92 percent / H2 / Pd-C / ethyl acetate / 12 h / Ambient temperature 3: Dess-Martin periodinane / CH2Cl2 / 0.17 h / Ambient temperature 4: 1) Zn, PPh3 / 1) CH2Cl2, 24 h, 2) CH2Cl2, 0 deg C, 2 h 5: 71 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C -> -30 deg C, 2) -30 deg C, 1 h View Scheme

1: 92 percent / H2 / Pd-C / ethyl acetate / 12 h / Ambient temperature 2: Dess-Martin periodinane / CH2Cl2 / 0.17 h / Ambient temperature 3: 1) Zn, PPh3 / 1) CH2Cl2, 24 h, 2) CH2Cl2, 0 deg C, 2 h 4: 71 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C -> -30 deg C, 2) -30 deg C, 1 h View Scheme

1: With 1H-imidazole 2: With methanol; potassium carbonate

1: 1) Zn, PPh3 / 1) CH2Cl2, 24 h, 2) CH2Cl2, 0 deg C, 2 h 2: 71 percent / n-BuLi / tetrahydrofuran; hexane / 1) -78 deg C -> -30 deg C, 2) -30 deg C, 1 h View Scheme

1: [(R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine](p-cymene)ruthenium / isopropyl alcohol 2: 1H-imidazole View Scheme