Diethyl Ether → HCID 15113981, compound

HRID 2249012Notes

Reaction equation

HRID 2249012 reaction equation
C(NC(C)C)(C)C.[FH:8].[F:9][C:10]1[C:15]([CH:16]2[O:18][CH2:17]2)=[C:14]([F:19])[C:13]([F:20])=[C:12]([F:21])[C:11]=1[F:22].C(OCC)C>O>[F:8][CH:16]([C:15]1[C:10]([F:9])=[C:11]([F:22])[C:12]([F:21])=[C:13]([F:20])[C:14]=1[F:19])[CH2:17][OH:18]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7912Diisopropylamine2×HCID 14917Hydrofluoric AcidHCID 27759812-(2,3,4,5,6-Pentafluorophenyl)oxirane

Product 1

HCID 15113981HCID 15113981, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. temperaturewas cooled in a dry-ice methanol bath
  2. extractionthe aqueous layer was extracted with 20 ml of ether
  3. washThe combined ether solution was washed with an aqueous solution of sodium carbonate
  4. dry with materialwater, and was dried over anhydrous sodium sulfate
  5. distillationAfter ether was distilled off
  6. distillationdistillation under reduced pressure
  7. custom(Kugelrohr, 70-80° C./15 mmHg)

Sources & evidence

ORD record
ord-a3ed02b2867f49769dbfcbf53997e444
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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