1: 95 percent / NaN3, NH4Cl / acetone; methanol / 20 h / Heating 2: 91 percent / DMAP / CH2Cl2 / 1 h / 23 °C 3: 93 percent / H2 / 10percent Pd-C / methanol / 4 h / 23 °C / 2585.7 Torr 4: aq. Na2CO3 / methanol / 4 h / 23 °C 5: ethyl acetate 6: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 7: 80 percent / 1N HCl / methanol / 2 h / Heating View Scheme

1: 95 percent / NaN3, NH4Cl / acetone; methanol / 20 h / Heating 2: 91 percent / DMAP / CH2Cl2 / 1 h / 23 °C 3: 93 percent / H2 / 10percent Pd-C / methanol / 4 h / 23 °C / 2585.7 Torr 4: aq. Na2CO3 / methanol / 4 h / 23 °C 5: ethyl acetate 6: 1) SOCl2 / 1) CHCl3, 45 deg C, 5 h, 2) CHCl3, reflux, 48 h 7: 80 percent / 1N HCl / methanol / 2 h / Heating 8: 80 percent / aq. K2CO3 / methanol / 12 h / 23 °C View Scheme