sulfuric acid

sodium tetrahydroborate in ethanol 18 h; Ambient temperature; Yield given;

1: 89 percent / O3 / methanol / -20 °C 2: NaBH4 / ethanol View Scheme

1: 91 percent / 93percent H2SO4 2: 96 percent / aq. NaOH / 7 h / Heating 3: 94 percent / H2SO4 View Scheme

1: 96 percent / aq. NaOH / 7 h / Heating 2: 94 percent / H2SO4 View Scheme

(i) O3, EtOH, (ii) NaBH4; Multistep reaction;

1: 54 percent / silver zeolite / CH2Cl2 / 40 h / Ambient temperature 2: 99 percent / methanol / 0.5 h View Scheme

1: 54 percent / silver zeolite / CH2Cl2 / 40 h / Ambient temperature 2: 99 percent / methanol / 0.5 h 3: 64 percent / p-TsOH*H2O / acetonitrile / 0.83 h / Ambient temperature 4: 90 percent / 1) NaH / tetrahydrofuran / 21 h / Ambient temperature 5: 1) sodium cyanoborohydride, mol. sieves 3A, 2) TFA / 1) DMF, 15 min, RT, 2) DMF, 43 h 6: 66 percent / silver triflate, collidine / nitromethane / 1) -25 deg C, 30 min, 2) RT, 4.5 h 7: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / Ambient temperature; 1) 0 deg C, 10 min, 2) RT, 45 min View Scheme

silver zeolite in dichloromethane 40 h; Ambient temperature;

1: pyridine / 0 °C 2: 6.2 g / LiI / acetone / 14 h / Heating View Scheme