sodium iodide in acetone 12 h; Heating; Yield given;

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 2: 93 percent / 1N NaOH / ethanol / 3 h / Ambient temperature 3: 100 percent / NaBH4*Et2O / tetrahydrofuran / -78 - 20 °C 4: triethylamine / CH2Cl2 / 1 h / -78 °C 5: NaI / acetone / 12 h / Heating View Scheme

1: 100 percent / NaBH4*Et2O / tetrahydrofuran / -78 - 20 °C 2: triethylamine / CH2Cl2 / 1 h / -78 °C 3: NaI / acetone / 12 h / Heating View Scheme

1: triethylamine / CH2Cl2 / 1 h / -78 °C 2: NaI / acetone / 12 h / Heating View Scheme

1: 93 percent / 1N NaOH / ethanol / 3 h / Ambient temperature 2: 100 percent / NaBH4*Et2O / tetrahydrofuran / -78 - 20 °C 3: triethylamine / CH2Cl2 / 1 h / -78 °C 4: NaI / acetone / 12 h / Heating View Scheme

(i) HCl, (ii) H2SO4, EtOH, (iii) NaI, acetone; Multistep reaction;