(R)-1-Chloro-6-trimethylsilanyl-hex-4-yn-2-ol → (Z)-(R)-1-chloro-6-trimethylsilanyl-hex-4-en-2-ol

Participants

Reaction Steps

13.04 g (63.7 mmol) of (R)-1-Chloro-6-trimethylsilanyl-hex-4yn-2-ol was dissolved in 260 ml of abs. EtOH and hydrogenated, in the presence of 9 drops of quinoline, over 1.70 g of Lindlar catalyst at ambient temperature and 1 atm of H2. The progress of the reaction was followed by GC. After 2 h the reaction mixture was filtered and the solvent removed i.V. Short flash chromatography (SiO2, hexane/AcOEt=85/15) afforded 12.97 g of (Z)-(R)-l-chloro-6-trimethylsilanyl-hex-4-en-2-ol as colorless oil.

Provenance & Evidence