1-(tert-butyldimethylsilyloxy)-1-methoxyethene; zinc(II) iodide in acetonitrile 6 h; Ambient temperature;

1: 67 percent / aq. KOH / ethanol / 1 h / Heating 2: 96 percent / (trimethylsilyl)ethoxyacetylene, HgO / 1,2-dichloro-ethane / 8 h / 60 °C 3: NaIO4 / methanol / Ambient temperature 4: 73 percent / 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene / ZnI2 / acetonitrile / 6 h / Ambient temperature View Scheme

1: 96 percent / (trimethylsilyl)ethoxyacetylene, HgO / 1,2-dichloro-ethane / 8 h / 60 °C 2: NaIO4 / methanol / Ambient temperature 3: 73 percent / 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene / ZnI2 / acetonitrile / 6 h / Ambient temperature View Scheme

1: 94 percent / Et3N / 1.) r.t., 5 min, 2.) 50 - 60 deg C, 1 h 2: 67 percent / aq. KOH / ethanol / 1 h / Heating 3: 96 percent / (trimethylsilyl)ethoxyacetylene, HgO / 1,2-dichloro-ethane / 8 h / 60 °C 4: NaIO4 / methanol / Ambient temperature 5: 73 percent / 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene / ZnI2 / acetonitrile / 6 h / Ambient temperature View Scheme

1: NaIO4 / methanol / Ambient temperature 2: 73 percent / 1-(dimethyl-tert-butylsiloxy)-1-methoxyethylene / ZnI2 / acetonitrile / 6 h / Ambient temperature View Scheme