sodium hydroxide; N,N-dimethyl acetamide in water T=20°C; pH=6; 48 h;

1.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 1.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 2.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 3.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

2: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1.1: 4.50 g / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 2.1: 90 percent / acetic acid / tetrahydrofuran; H2O / 12 h / 20 °C 3.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 4.1: ozone / CH2Cl2 / 0.5 h / -78 °C 4.2: 76 percent / NaBH4 / CH2Cl2; methanol 5.1: 100 percent / NaIO4 / H2O; tetrahydrofuran / 1.25 h / 0 - 20 °C 6.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 7.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 8.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 9.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 9.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 10.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 11.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 12.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 13.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 13.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 14.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 15.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 2.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 3.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 4.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 4.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 5.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 6.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 7.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 8.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 9.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 10.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 2.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 3.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 3.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 4.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 5.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 6.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 7.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 8.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 9.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 100 percent / NaIO4 / H2O; tetrahydrofuran / 1.25 h / 0 - 20 °C 2.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 3.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 4.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 5.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 5.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 6.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 7.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 8.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 9.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 10.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 11.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 2.1: ozone / CH2Cl2 / 0.5 h / -78 °C 2.2: 76 percent / NaBH4 / CH2Cl2; methanol 3.1: 100 percent / NaIO4 / H2O; tetrahydrofuran / 1.25 h / 0 - 20 °C 4.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 5.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 6.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 7.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 7.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 8.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 9.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 10.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 11.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 12.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 13.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: ozone / CH2Cl2 / 0.5 h / -78 °C 1.2: 76 percent / NaBH4 / CH2Cl2; methanol 2.1: 100 percent / NaIO4 / H2O; tetrahydrofuran / 1.25 h / 0 - 20 °C 3.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 4.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 5.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 6.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 6.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 7.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 8.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 9.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 10.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 11.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 12.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme

1.1: 90 percent / acetic acid / tetrahydrofuran; H2O / 12 h / 20 °C 2.1: 85 percent / NaBH4 / methanol / 0.5 h / 0 °C 3.1: ozone / CH2Cl2 / 0.5 h / -78 °C 3.2: 76 percent / NaBH4 / CH2Cl2; methanol 4.1: 100 percent / NaIO4 / H2O; tetrahydrofuran / 1.25 h / 0 - 20 °C 5.1: 83 percent / pyridinium chlorochromate; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 20 °C 6.1: 38 percent / BF3*Et2O / CH2Cl2 / 25 h / 0 - 20 °C 7.1: 99 percent / 2,6-lutidine / CH2Cl2 / -20 - 20 °C 8.1: HMPA; t-BuLi / tetrahydrofuran; hexane / 1.5 h / -50 - -43 °C 8.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -50 °C 9.1: pyridine; 4-(dimethylamino)pyridine / 20 °C 10.1: DDQ / CH2Cl2; H2O; toluene / 1 h / 20 °C 11.1: 24.7 mg / CaCO3 / methanol / 7 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 5 h / 20 °C 12.2: 84 percent / 4-(dimethylamino)pyridine / toluene / 0.5 h / 20 °C 13.1: pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 12 h / 20 °C 14.1: 8.0 mg / mercury(II) perchlorate trihydrate; calcium carbonate / acetonitrile; H2O / 0.05 h / 20 °C View Scheme