4-Toluenesulfonyl chloride → HCID 54277958, compound

Participants

Reaction Steps

28.5 g (0.113 mol) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethanol were dissolved in 150 ml of pyridine and treated portionwise within 30 minutes at 0° with 31.5 g (0.165 mol) of p-toluenesulphonyl chloride. After 90 minutes the reaction solution was poured into ice-water and extracted with ether. The organic phase was washed in succession with 3N hydrochloric acid, water and a saturated sodium carbonate solution. After drying over magnesium sulphate and evaporation of the solvent under reduced pressure, the remaining oily residue was recrystallized from ether/hexane, yielding 38.8 g (85%) of [1R,2R]-(-)-2-[6-fluoro-1,2,3,4-tetrahydro-2-hydroxy-1-isopropyl-2-naphthyl]ethyl p-toluenesulphonate as white crystals, m.p. 65°-67°; [α]D20 =-54.1° (c=1, methanol).

Provenance & Evidence