Dimethyl Sulfoxide → 2-(Trifluoromethyl)-5-(2-methyloxiran-2-yl)pyridine

HRID 1045550Notes

Reaction equation

HRID 1045550 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1>C1COCC1>[F:24][C:13]([F:23])([F:12])[C:14]1[CH:15]=[CH:16][C:17]([C:20]2([CH3:8])[CH2:21][O:22]2)=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 218805781-[6-(Trifluoromethyl)pyridin-3-yl]ethan-1-one

Product 1

HCID 594549782-(Trifluoromethyl)-5-(2-methyloxiran-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

The title compound was prepared by following general procedure 3. DMSO was added to NaH (1 equiv.) and heated to 65° C. for 1 h. THF was added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1 equiv.) was added and stirred for 10 min. after which the solution of 1-(6-(trifluoromethyl)pyridin-3-yl)ethanone (1 equiv.) in THF was added dropwise. After complete addition, the reaction mixture was stirred at RT for 2 h. The product was detected by LCMS and the reaction mixture was poured into ice water, extracted in diethyl ether (4×50 mL), dried over Na2SO4 and concentrated at 25° C. to obtain the product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture was cooled to 0° C
  3. additionwas added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether (4×50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated at 25° C.
  8. customto obtain the product

Sources & evidence

ORD record
ord-f3b1aeb7eeb9473589d165b59e3f29b3
Source dataset
uspto-grants-2013_10
Patent number
US08569287B2

Reaction notes

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