1: 1-bromo-butane With magnesium in tetrahydrofuran 2: (RS)-15-methylpentacosanal in tetrahydrofuran T=0 - 20°C; Grignard reaction; 1 h;

1.1: magnesium; iodine / tetrahydrofuran / 60 °C 1.2: 38 percent / tetrahydrofuran / 48 h / cooling 2.1: pyridine / CH2Cl2 / 72 h / cooling 3.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / Heating 4.1: 1.52 g / hydrochloric acid / H2O / 0.5 h / Heating 5.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 6.1: magnesium / tetrahydrofuran 6.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

1.1: 99 percent / periodic acid dihydrate / tetrahydrofuran / 1 h / 0 - 5 °C 2.1: magnesium; iodine / tetrahydrofuran / 60 °C 2.2: 38 percent / tetrahydrofuran / 48 h / cooling 3.1: pyridine / CH2Cl2 / 72 h / cooling 4.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / Heating 5.1: 1.52 g / hydrochloric acid / H2O / 0.5 h / Heating 6.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 7.1: magnesium / tetrahydrofuran 7.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

1.1: 12.1 g / osmium tetroxide; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H2O; acetone / 72 h / 20 °C 2.1: 99 percent / periodic acid dihydrate / tetrahydrofuran / 1 h / 0 - 5 °C 3.1: magnesium; iodine / tetrahydrofuran / 60 °C 3.2: 38 percent / tetrahydrofuran / 48 h / cooling 4.1: pyridine / CH2Cl2 / 72 h / cooling 5.1: lithium aluminum hydride / tetrahydrofuran / 1.5 h / Heating 6.1: 1.52 g / hydrochloric acid / H2O / 0.5 h / Heating 7.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 8.1: magnesium / tetrahydrofuran 8.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

1.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 2.1: magnesium / tetrahydrofuran 2.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

1.1: 1.52 g / hydrochloric acid / H2O / 0.5 h / Heating 2.1: 73.5 percent / sodium acetate; molecular sieves 4 Angstroem; pyridinium chlorochromate / CH2Cl2 / 2.33 h / 0 - 20 °C 3.1: magnesium / tetrahydrofuran 3.2: 73 percent / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme