Potassium Carbonate → 5-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine

HRID 623478Notes

Reaction equation

HRID 623478 reaction equation
CC1C=CC(S(O[CH2:12][CH:13]([OH:26])[C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:26]1[CH2:12][CH:13]1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:23])([F:24])[F:25])=[N:16][CH:15]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 874265272-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 874265125-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridineYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate (1.66 g, 4.25 mmol, Step-4, single enantiomer) and potassium carbonate (1.76 g, 12.8 mmol) in methanol (43 mL) is stirred at room temperature for 2 hours. White precipitate is filtrated and filtrate is concentrated in vacuo. The residue is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo to give 0.89 g (95% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-6) without further purification.

Workup

  1. filtrationWhite precipitate is filtrated
  2. concentrationfiltrate is concentrated in vacuo
  3. additionThe residue is poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-481166b934a54a6fb365ab5304310a0a
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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