sodium in tetrahydrofuran; tert-butyl alcohol 24 h; Heating;

1: 40 percent / toluene / 24 h / Heating 2: 10 percent / Na / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / Heating View Scheme

1: CeCl3, NaBH4 / methanol / 2 h / 0 °C 2: 80 percent / Et3N / CH2Cl2 / 1 h / 0 °C 3: 105 mg / NaI / acetone / 15 h / Heating 4: 40 percent / toluene / 24 h / Heating 5: 10 percent / Na / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / Heating View Scheme

1: 80 percent / Et3N / CH2Cl2 / 1 h / 0 °C 2: 105 mg / NaI / acetone / 15 h / Heating 3: 40 percent / toluene / 24 h / Heating 4: 10 percent / Na / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / Heating View Scheme

2: CeCl3, NaBH4 / methanol / 2 h / 0 °C 3: 80 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 105 mg / NaI / acetone / 15 h / Heating 5: 40 percent / toluene / 24 h / Heating 6: 10 percent / Na / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / Heating View Scheme

2: CeCl3, NaBH4 / methanol / 2 h / 0 °C 3: 80 percent / Et3N / CH2Cl2 / 1 h / 0 °C 4: 105 mg / NaI / acetone / 15 h / Heating 5: 40 percent / toluene / 24 h / Heating 6: 10 percent / Na / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / Heating View Scheme