Diethyl Ether → HCID 15113981, compound

Participants

Reaction Steps

A Teflon vessel containing 2.7 g (22.5 mmol) of diisopropylamine was cooled in a dry-ice methanol bath, and to this was added dropwise 1.8 g (90 mmol) of anhydrous hydrogen fluoride to prepare 4.5 g (22.5 mmol) of (i-Pr)2NH. 4HF. To this was added dropwise 3.15 g (15 mmol) of (+)-pentafluorostyrene oxide at 0° C. and the resulted mixture was stirred for 30 hours under N2 at room temperature. To this was added 30 ml of diethyl ether and 30 ml of water and the aqueous layer was extracted with 20 ml of ether. The combined ether solution was washed with an aqueous solution of sodium carbonate and then water, and was dried over anhydrous sodium sulfate. After ether was distilled off, distillation under reduced pressure was carried out (Kugelrohr, 70-80° C./15 mmHg), thereby obtaining 1.0 g of (+)-2-fluoro-2-(pentafluorophenyl)ethanol. The yield was 29%, the GC purity was 98%, and [α]D25 was +12.0° (c=0.30, CHCl3). The other physical properties were mentioned above.

Provenance & Evidence