1: 1.) LiAlH4; 2.) HCl / 1.) ether, 30 min; 2.) MeOH-H2O, pH=4, 3 h 2: sodium periodate / ethanol / 0.33 h / Ambient temperature 3: 38 percent / MeOOCN(1-)SO2N(1+)Et3 / benzene / 1 h / 70 °C View Scheme

1: 2.) 6N HCl / 1.) ether, THF, -79 deg C, 1 h; 2.) MeOH, -30 deg C, 3 h 2: 91 percent / NaIO4 / ethanol / 0.25 h 3: 80 percent / MeOOCN(1-)SO2N(1+)Et3 / benzene / 2 h / 50 °C View Scheme