Dimethyl Sulfoxide → HCID 59455178, compound

HRID 1481380Notes

Reaction equation

HRID 1481380 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=1[C:21](=[O:23])[CH3:22]>C1COCC1>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[C:14]=1[C:21]1([CH3:8])[CH2:22][O:23]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 27769062',4',6'-Trifluoroacetophenone

Product 1

HCID 59455178HCID 59455178, compound

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-(2,4,6-trifluorophenyl)ethanone (1 equiv.) in THF was added dropwise. After completion of this 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 with 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 completion of this addition
  5. extractionextracted with 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-b43596f7863b4788a62f974f283c2f09
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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