methanol; water; toluene-4-sulfonic acid in diethyl ether

lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;

1: 88 percent / triethylamine; DMAP / tetrahydrofuran; CH2Cl2 / 1 h / 0 - 20 °C 2: 72 percent / PTSA / methanol / 3 h / 20 °C 3: 70 percent / PCC / CH2Cl2 / 3 h / 0 - 20 °C 4: 65 percent / toluene / 12 h / Heating 5: 82 percent / NaBH4 / methanol / 1 h / 0 - 20 °C 6: 65 percent / conc. HCl; MnO2 / tetrahydrofuran / 0.5 h / -10 °C 7: 80 percent / DMF; thionyl chloride / CHCl3 / 3 h / 20 °C 8: 40 percent / pyridine / acetonitrile / 12 h / 20 °C 9: 40 percent / sodium acetate / acetic acid / 20 h / 20 °C 10: 68 percent / sodium acetate; hydrogen / Pd(OH)2/C / ethanol / 24 h / 20 °C 11: 66 percent / NaOMe / methanol / 10 h / 20 °C 12: 60 percent / PCC; celite / CH2Cl2 / 12 h / 20 °C View Scheme