sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene in tert-butyl alcohol T=20°C; 3 h;

1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 2: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 3: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C 4: 96 percent / NaClO2; 2-methyl-2-butene; aq. NaH2PO4 / 2-methyl-propan-2-ol / 3 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C 2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C 5.1: 96 percent / NaClO2; 2-methyl-2-butene; aq. NaH2PO4 / 2-methyl-propan-2-ol / 3 h / 20 °C View Scheme

1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 2: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C 3: 96 percent / NaClO2; 2-methyl-2-butene; aq. NaH2PO4 / 2-methyl-propan-2-ol / 3 h / 20 °C View Scheme

3: 98 percent / H+ / methanol 4: 98 percent / H2 / Lindlar catalyst / hexane / 759.81 Torr 5: Jones' reagent / acetone View Scheme

pyridine; methanol; palladium on activated charcoal Hydrogenation;

1: ethanol / Erhitzen des Reaktionsprodukts mit wss.Natronlauge 2: Raney nickel; ethanol / Hydrogenation View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C 2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C 3.1: H2 / Lindlar's catalyst / hexane / 9 h / 20 °C 4.1: 8.7 g / (COCl)2; DMSO; Et3N / CH2Cl2 / 1 h / 0 °C 5.1: 96 percent / NaClO2; 2-methyl-2-butene; aq. NaH2PO4 / 2-methyl-propan-2-ol / 3 h / 20 °C View Scheme

1: ammonia 2: ethanol / Erhitzen des Reaktionsprodukts mit wss.Natronlauge 3: Raney nickel; ethanol / Hydrogenation View Scheme

1: methanol; toluene-4-sulfonic acid / 2 h / 20 °C 2: Jone's reagent / acetone / 0.33 h / 0 - 20 °C View Scheme