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

HRID 1400359Notes

Reaction equation

HRID 1400359 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[C:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]([F:24])([F:23])[F:22])=[N:19][CH:20]=1)(=[O:14])[CH3:13]>C1COCC1>[F:23][C:21]([F:24])([F:22])[C:18]1[CH:17]=[CH:16][C:15]([C:12]2([CH3:8])[CH2:13][O:14]2)=[CH:20][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

DMSO is added to NaH (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents stirred for 10 min. after which the solution of 5-acetyl-2-(trifluoromethyl)pyridine (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h; the reaction is monitored by LCMS. After completion, the reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get the crude product.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionis added dropwise
  4. additionAfter complete addition
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Sources & evidence

ORD record
ord-0a522a32ad324c979462f2861a4a2a91
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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