methyl iodide in water; acetone 5 h; Heating;

1: 69.3 percent / glacial acetic acid, 20percent H2SO4 / H2O / 2 h / 120 °C 2: 82.3 percent / boron trifluoride etherate / CH2Cl2 / 2 h / Ambient temperature 3: 1.) sodium hydride / 1,2-dimethoxy-ethane / 1.) 0.5 h, 70 deg, 2.) 1 h, reflux 4: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 5: 44.3 percent / pyridine / 8 h / Ambient temperature 6: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 7: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 82.3 percent / boron trifluoride etherate / CH2Cl2 / 2 h / Ambient temperature 2: 1.) sodium hydride / 1,2-dimethoxy-ethane / 1.) 0.5 h, 70 deg, 2.) 1 h, reflux 3: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 4: 44.3 percent / pyridine / 8 h / Ambient temperature 5: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 6: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 1.) sodium hydride / 1,2-dimethoxy-ethane / 1.) 0.5 h, 70 deg, 2.) 1 h, reflux 2: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 3: 44.3 percent / pyridine / 8 h / Ambient temperature 4: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 5: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 44.3 percent / pyridine / 8 h / Ambient temperature 2: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 3: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 2: 44.3 percent / pyridine / 8 h / Ambient temperature 3: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 4: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 1.) n-butyl-lithium / 1.) ether, 4 h, -15 deg C, 2.) 2 h, -15 deg C 2: 69.3 percent / glacial acetic acid, 20percent H2SO4 / H2O / 2 h / 120 °C 3: 82.3 percent / boron trifluoride etherate / CH2Cl2 / 2 h / Ambient temperature 4: 1.) sodium hydride / 1,2-dimethoxy-ethane / 1.) 0.5 h, 70 deg, 2.) 1 h, reflux 5: 79.5 percent / sodium borohydride / methanol / 1 h / Ambient temperature 6: 44.3 percent / pyridine / 8 h / Ambient temperature 7: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 8: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

1: 33.6 percent / lithium bromide / dimethylformamide / 5 h / 80 °C 2: 78.7 percent / methyl iodide / H2O; acetone / 5 h / Heating View Scheme

2: Al(OiPr)3 View Scheme

aluminum isopropoxide