in tetrahydrofuran 0.5 h;

1: 58 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C 2: 88 percent / tetrahydrofuran / 0.5 h / 20 °C View Scheme

1: 86 percent / sodium hydride / dimethylformamide / 20 h / 20 °C 2: 58 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C 3: 88 percent / tetrahydrofuran / 0.5 h / 20 °C View Scheme

in tetrahydrofuran T=0 - 20°C; Inert atmosphere;

Grignard reaction;

1.1: propionic acid / xylene / 2.5 h / Heating 2.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 3.1: KOH / H2O; methanol / 2 h / 60 °C 4.1: 13.52 g / TsOH / CH2Cl2 5.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C 6.1: 98 percent / H2; propionic acid / methanol / 16 h 7.1: PCC; Celite / CH2Cl2 / 2 h / 20 °C 8.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 8.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 9.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 11.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 12.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 13.1: 81 percent / pyridine / 3 h / Heating 14.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 15.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 16.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 17.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 18.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 19.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 20.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 20.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 21.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 22.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme