1: 1-(mercaptomethyl)-cyclopropaneacetic acid With caesium carbonate in N,N-dimethyl-formamide T=20°C; 0.25 h; 2: 2-[2-[(3S)-[3-[(2E)-(7-chloroquinolin-2-yl)ethenyl]phenyl]-3-chloropropyl]phenyl]-2-propanol in N,N-dimethyl-formamide T=30 - 55°C; 2 - 3 h; Product distribution / selectivity;

1: 1-(mercaptomethyl)-cyclopropaneacetic acid With n-butyllithium in tetrahydrofuran; hexane T=-12.5°C; 1 h; Inert atmosphere; 2: 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran; hexane T=-12.5 - -2.5°C; 6 h; Saturated solution; 3: With water; sodium chloride in tetrahydrofuran; hexane T=2.5 - 30°C; Product distribution / selectivity;

1.1: sodium hydride / N,N-dimethyl-formamide / -5 - 0 °C / Inert atmosphere 1.2: 20 - 45 °C 2.1: dichloromethane; water 2.2: 25 - 35 °C 3.1: cerium(III) chloride / tetrahydrofuran / -5 - 65 °C / Inert atmosphere View Scheme

1: 1-(mercaptomethyl)-cyclopropaneacetic acid With sodium t-butanolate; PEG-600 in toluene T=-10°C; Inert atmosphere; 2: 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)-ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol methanesulfonate in tetrahydrofuran; toluene T=-10 - 20°C;

1.1: sodium hydride / N,N-dimethyl-formamide / -5 - 0 °C / Inert atmosphere 1.2: 20 - 45 °C 2.1: dichloromethane; water 2.2: 25 - 35 °C 3.1: cerium(III) chloride / tetrahydrofuran / -5 - 65 °C / Inert atmosphere 4.1: sodium hydroxide / ethanol; water; methanol / 25 - 50 °C View Scheme

sodium t-butanolate in tetrahydrofuran; toluene T=-10 - 21°C; Inert atmosphereLarge scale reaction;

sodium t-butanolate in tetrahydrofuran; toluene T=-10 - 20°C; Inert atmosphereLarge scale reaction;

thionyl chloride T=0 - 65°C;

1: 1-(mercaptomethyl)-cyclopropaneacetic acid With sodium t-butanolate; PEG-600 in toluene Inert atmosphere; 2: montelukast sodium salt in tetrahydrofuran; toluene T=20°C; Inert atmosphere;