2-(2,3,4,5,6-pentafluorophenyl)oxirane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To Teflon vessel containing 4.2 g (22.5 mmol)of tributylamine was cooled in a dry-ice methanol bath, and to this was added dropwise 2.3 g (112.5 mmol) of anhydrous hydrogen fluoride to prepare 6.4 g (22.5 mmol) of n-Bu3N.5HF. To this was added dropwise 3.15 g (15 mmol) of (+)-pentafluorostyrene oxide at 0° C., and was stirred for 10 hours at 40° C. After it was left to cool, the same treatment as that provided in Example 16 gave 1.1 g of (+)-2-fluoro-2-(pentafluorophenyl)ethanol. Its GC purity was 96%, while its [α]D25 was +10.8° (c=0.54, CHCl3). was cooled in a dry-ice methanol bath After it was left to cool the same treatment as that provided in Example 16

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. was cooled in a dry-ice methanol bath the aqueous layer was extracted with 20 ml of ether The combined ether solution was washed with an aqueous solution of sodium carbonate water, and was dried over anhydrous sodium sulfate After ether was distilled off distillation under reduced pressure (Kugelrohr, 70-80° C./15 mmHg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10.5 g of (+)-2,3,4,5,6-pentafluorostyrene oxide (over 95%ee) in 50 ml of dichloromethane was added dropwise to 100 ml of a 1.0M solution of trimethylaluminum in hexane, and was reacted for 40 hours at room temperature. This reaction mixture was poured into 100 ml of 1N hydrochloric acid. After the aqueous layer was extracted with ether, the total organic solution was dried over magnesium sulfate. The solvent was distilled out under reduced pressure, and the subsequent distillation under reduced pressure gave 10.6 g of (+)-2-(pentafluorophenyl)-1-propanol having the aforementioned physical properties. was reacted for 40 hours at room temperature After the aqueous layer was extracted with ether the total organic solution was dried over magnesium sulfate The solvent was distilled out under reduced pressure the subsequent distillation under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 10.5 g of (+)-2,3,4,5,6-pentafluorostyrene oxide (over 95%ee) in 50 ml of dichloromethane was added dropwise to 100 ml of a 1.0M solution of trimethylaluminum in hexane, and was reacted for 40 hours at room temperature. This reaction mixture was poured into 100 ml of 1N hydrochloric acid. After the aqueous layer was extracted with ether, the total organic solution was dried over magnesium sulfate. The solvent was distilled out under reduced pressure, and the subsequent distillation under reduced pressure gave 10.6 g of (+)-2-(pentafluorophenyl)-1-propanol having the aforementioned physical properties. was reacted for 40 hours at room temperature After the aqueous layer was extracted with ether the total organic solution was dried over magnesium sulfate The solvent was distilled out under reduced pressure the subsequent distillation under reduced pressure