1: methyl-magnesium chloride With cerium(III) chloride in tetrahydrofuran T=-5 - 0°C; 2.75 h; 2: [R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl) ethenyl]phenyl]-3-[2-(methylcarbonyl)phenyl] propyl]thio]methyl]cyclopropane acetic acid in tetrahydrofuran; toluene T=-5 - 0°C; 2 h; 3: With water in tetrahydrofuran; toluene T=0°C; Product distribution / selectivity;

1: With sodium methylate in tetrahydrofuran; methanol T=20°C; 22.1667 h; 2: With sodium hydroxide; water in tetrahydrofuran; methanol T=55°C; 1.75 h; 3: With acetic acid in toluene pH=5; 0.25 h;

acetic acid in dichloromethane; water pH=5.0 - 6.0; 0.166667 h; Product distribution / selectivity;

1.1: sodium methylate / methanol; N,N-dimethyl-formamide / 1.5 h / -5 - 0 °C 1.2: 19 h / 0 - 5 °C 2.1: tetrahydrofuran / 9 h / 0 - 5 °C View Scheme

1.1: B-chloro-diisopinocampheylborane / dichloromethane / -5 - 0 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 5 °C 3.1: sodium methylate / methanol; N,N-dimethyl-formamide / 1.5 h / -5 - 0 °C 3.2: 19 h / 0 - 5 °C 4.1: tetrahydrofuran / 9 h / 0 - 5 °C View Scheme

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 5 °C 2.1: sodium methylate / methanol; N,N-dimethyl-formamide / 1.5 h / -5 - 0 °C 2.2: 19 h / 0 - 5 °C 3.1: tetrahydrofuran / 9 h / 0 - 5 °C View Scheme

in tetrahydrofuran T=0 - 5°C; Grignard reaction; 9 h;