1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: With zinc(II) chloride in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphere; 3: EtZnCl; 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

1: (4-methoxymethoxy)phenylphenylacetylene With Me3SnLi in tetrahydrofuran; hexane T=0°C; 3 h; Inert atmosphere; 2: ethyl iodide in tetrahydrofuran; hexane T=0 - 20°C; 3 h; Inert atmosphere; 3: 2-(4-iodophenoxy)-N,N-dimethylethanamine stereoselective reactionFurther stages;

1: 1.) NaH / 1.) DMF, 2.) DMF 2: 82 percent / 48percent aq. HBr, acetic acid / 4 h / Heating 3: 98percent H2SO4 / 12 h / Ambient temperature 4: 1.) C2H5MgBr, 3.) HCl View Scheme

1: 85 percent / NaH, DMF / 3 h / 85 - 90 °C 2: 1.) C2H5MgBr, 3.) HCl View Scheme

1: 82 percent / 48percent aq. HBr, acetic acid / 4 h / Heating 2: 98percent H2SO4 / 12 h / Ambient temperature 3: 1.) C2H5MgBr, 3.) HCl View Scheme

1: 98percent H2SO4 / 12 h / Ambient temperature 2: 1.) C2H5MgBr, 3.) HCl View Scheme

hydrogenchloride; ethylmagnesium bromide Yield given. Multistep reaction. Yields of byproduct given;