1: 98 percent / K2CO3 / acetonitrile 2: NaBH4 / ethanol 3: PBr3 / CH2Cl2 4: 76 percent / LiHMDS / tetrahydrofuran 5: 81 percent / LiOH; H2O2 6: 95 percent / LAH / tetrahydrofuran 7: 97 percent / PPh3; NBS / CH2Cl2 8: 68 percent / n-BuLi 9: HCl / acetonitrile 10: Et3N 11: NaBH4 / ethanol 12: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2 13: Mg 14: 23 percent / H2 / Pd(OH)2/C 15: 38 percent / TPAP; NMMO 16: 65 percent / 2-hydroxypyridine; Et3N 17: TMSCl; phenol / CH2Cl2 View Scheme

2: hydrogen / PtO2 / ethanol / 2.3 h / 2250.2 Torr View Scheme

1: 94 percent / K2CO3 / ethanol / 5 h / Heating 2: 88 percent / NH4OAc; AcOH / 4 h / Heating 3: 63 percent / LiAlH4 / diethyl ether; tetrahydrofuran / 2 h / Heating 4: 5percent aq. NaOH / CH2Cl2 / 2 h / 20 °C 5: conc. HCl / ethanol / 4 h / Heating View Scheme

1: diethyl ether / 3 h / Heating 2: glacial acetic acid / 3 h / Heating View Scheme

propionic acid sodium salt Erwaermen des Reaktionsprodukts mit aethanol. KOH;

Heating;

1.1: 75 percent / Br2; Fe; NaOAc / acetic acid / 1 h / 20 °C 2.1: [(ν3-C3H5)PdCl]2; (1S,2S)-bis(N,N'-(o-(PPh2)C6H4CO)-1,2-diphenylethylamine; Et3N / CH2Cl2 / 8 h / 20 °C 3.1: TsOH*H2O / methanol / 4 h / 50 °C 4.1: DIBAlH / toluene; hexane / 1.5 h / -78 °C 5.1: Ph3P; diisopropylazodicarboxylate / diethyl ether / 0.33 h / -20 °C 5.2: diethyl ether / 12 h / -20 - 20 °C 5.3: 1.34 g / aq. TsOH / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 24 h / 107 °C 7.1: 91 percent / PPh3 / CH2Cl2 / 0.17 h / 0 °C 8.1: 88 percent / Pd(PPh3)4; Bu3SnH / toluene / 0.33 h 9.1: 65 percent / Pd(OAc)2; Ag2CO3; diphenylphosphinopropane / 1,3-bis(diphenylphosphino)propane / toluene / 4 h / 107 °C 10.1: SeO2; quartz sand / dioxane / 1.33 h / 75 °C 11.1: DIBALH / CH2Cl2; hexane; diethyl ether / -78 - 0 °C 11.2: NH4Br / various solvents / 2 h / 20 °C 11.3: 89 percent / NaBH4 / various solvents / 20 °C 12.1: LDA / tetrahydrofuran; hexane / -78 - 20 °C 12.2: 57 percent / tetrahydrofuran; hexane / 6 h / 20 °C / Irradiation 13.1: BBr3 View Scheme

potassium iodide; potassium carbonate in N-methyl-acetamide; toluene

caesium carbonate in ethylene glycol dimethyl ether T=145°C; 0.416667 h; Microwave irradiationInert atmosphereSealed vessel;

potassium carbonate in acetone Etherification; methylation; 0.0833333 h; microwave irradiation;