Hydrochloric Acid → 3-Trifluoromethyl-1.5-pentanediol

Participants

Reaction Steps

12.0 g (59.97 mmol) of 3-(trifluoromethyl)pentanedioic acid were dissolved in 70 ml of abs. THF, and, after cooling to −10° C., 120 ml (120 mmol) of a 1 M solution of lithium aluminium hydride in THF were added dropwise. After the addition had ended, the reaction mixture was warmed to RT overnight. After cooling to 0° C., initially about 10 ml of isopropanol and then 20 ml of an isopropanol/water mixture (3:1) were carefully added dropwise. The resulting suspension was acidified by addition of 1 N hydrochloric acid and mixed with Celite. The mixture was filtered and the filtrate obtained was concentrated under reduced pressure. To remove residual water, acetonitrile was added to the oil obtained and the mixture was once more concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 4:1→1:1). This gave 4.5 g of the target product (43.6% of theory).

Provenance & Evidence