trimethyl iodide in chloroform T=60°C; 15 h;

1: 48 h / Heating 2: 1.) disiamylborane, 2.) H2O2 / 1.) THF, 0 deg C, then 25 deg C, 0.5 h, 2.) 0 deg C, aq. NaOH, 50 deg C, 1 h 3: Jones reagent / acetone / 0.17 h / 25 °C 4: 98 percent / trimethyl iodide / CHCl3 / 15 h / 60 °C View Scheme

1: 1.) disiamylborane, 2.) H2O2 / 1.) THF, 0 deg C, then 25 deg C, 0.5 h, 2.) 0 deg C, aq. NaOH, 50 deg C, 1 h 2: Jones reagent / acetone / 0.17 h / 25 °C 3: 98 percent / trimethyl iodide / CHCl3 / 15 h / 60 °C View Scheme

1: Jones reagent / acetone / 0.17 h / 25 °C 2: 98 percent / trimethyl iodide / CHCl3 / 15 h / 60 °C View Scheme

1.1: tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl-(2′-methyl-biphenyl-2-yl)-phosphane; potassium phosphate / ethylene glycol dimethyl ether / 14 h / 50 °C / |Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2.5 h / 20 °C / |Inert atmosphere 3.1: NiCl6H2O; sodium tetrahydroborate / methanol / 0.5 h / 0 °C / |Cooling with ice 3.2: 2 h / 20 °C View Scheme

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2.5 h / 20 °C / |Inert atmosphere 2.1: NiCl6H2O; sodium tetrahydroborate / methanol / 0.5 h / 0 °C / |Cooling with ice 2.2: 2 h / 20 °C View Scheme