(i) Raney-Ni, THF, (ii) Raney-Ni, (iii) KOH, aq. EtOH; Multistep reaction;

tetra-N-butylammonium borohydride in chloroform 12 h; Heating; Yields of byproduct given;

1: iodobenzene With chloro-trimethyl-silane; ethylene dibromide; zinc in tetrahydrofuran 2: S-ethyl cyclohexanecarbothioate With bis(acetylacetonate)nickel(II) in tetrahydrofuran; toluene T=20°C; 20 h;

1: 5-Iodo-pentanoic acid ethyl ester With chloro-trimethyl-silane; ethylene dibromide; zinc in tetrahydrofuran T=35°C; 0.5 h; 2: S-ethyl cyclohexanecarbothioate With bis(acetylacetonate)nickel(II) in tetrahydrofuran; toluene T=20°C; 20 h;

2: benzene 3: aq. NaOH / methanol View Scheme