aluminium trichloride in dichloromethane Friedel-Crafts acylation; 3 h; Heating;

AlCl3, aluminium chloride T=0 - 20°C; 12 h;

1: 99 percent / K2CO3 / acetonitrile / 0.83 h / 85 °C / microwave irradiation 2: 97 percent / aq. NaOH / toluene / 0.83 h / 80 °C / microwave irradiation View Scheme

1: 94 percent / dimethylformamide / 4 h / Ambient temperature 2: 69 percent / 1 M aq. HCl / methanol / 5 h / 40 °C View Scheme

1: (2S,3S,4R)-2-Ph2P(O)CH2-3-OH-4-(2-OH-4,5-F2-C6H2)tetraHpyran; Gd(HMDS)3; propionitrile / 3 h / -40 °C 2: 87 percent / DIBALH / toluene / 2 h / -78 - -40 °C 3: 98 percent / aq. HCl / tetrahydrofuran / 0.08 h / 20 °C 4: 97 percent / NaBH4 / tetrahydrofuran; H2O / 1.5 h / cooling 5: 74 percent / K2CO3 / acetonitrile / 3 h / Heating View Scheme

1.1: magnesium / tert-butyl methyl ether / 4 h / 55 °C 1.2: -10 - 0 °C 1.3: 3 h / 25 - 50 °C 2.1: sodium hydroxide / dimethyl sulfoxide / 5 h / 25 - 30 °C 3.1: water; lithium chloride; sodium tetrahydroborate / isopropyl alcohol / 20 h / -5 - 30 °C 3.2: pH 1 4.1: sodium hydrogencarbonate / toluene / 24 h / -15 °C / Enzymatic reaction 5.1: sodium hydrogencarbonate; iodine / ethyl acetate / 5 h / -15 °C 6.1: dimethyl sulfoxide / 24 h / 25 - 90 °C 6.2: 3 h / 25 - 30 °C 7.1: hydrogenchloride / tert-butyl methyl ether; acetone / 0.5 h / 25 - 30 °C 8.1: triethylamine / dichloromethane / 1 h / 12 - 22 °C 8.2: 4 h / 12 - 25 °C 9.1: 2,6-di-tert-butyl-4-methyl-phenol; sodium hydroxide; water / dimethyl sulfoxide / 0.17 h / 30 °C 9.2: 32 °C 10.1: 1,1'-carbonyldiimidazole / dichloromethane / 2 h / -10 °C / Inert atmosphere 10.2: 22 h / 0 - 30 °C 11.1: N,O-bis-(trimethylsilyl)-acetamide; 1H-imidazole; trimethylsilyl iodide / dichloromethane; isopropanol acetate / 19 h / 89 °C 11.2: 50 - 60 °C View Scheme

tributyl-amine; bis-triphenylphosphine-palladium(II) chloride T=110°C; P=7500.6 Torr; 2 h;

1: potassium carbonate / acetonitrile / 60 °C 2: sodium hydroxide / toluene / 4 h / 60 °C 3: potassium carbonate / acetonitrile / 60 °C View Scheme

1: 99 percent / (S)-2-methyl-CBS-OAB; BH3*C6H5N(C2H5)2 / various solvent(s); toluene / 11 h / 40 °C 2: 89 percent / NaOH / methanol / Heating View Scheme

1: 99 percent / K2CO3 / acetonitrile / 0.83 h / 85 °C / microwave irradiation 2: 97 percent / aq. NaOH / toluene / 0.83 h / 80 °C / microwave irradiation View Scheme