Dimethyl Sulfoxide → HCID 59455075, compound

HRID 1400356Notes

Reaction equation

HRID 1400356 reaction equation
CS(C)=O.[H-].[Na+].[I-].C[S+](C)C.[F:12][C:13]1[CH:18]=[CH:17][C:16](C(=O)C)=[CH:15][CH:14]=1.[CH2:22]1[CH2:26][O:25][CH2:24][CH2:23]1>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:24]2([CH3:23])[CH:26]([CH3:22])[O:25]2)=[CH:15][CH:14]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8028Tetrahydrofuran2×HCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 59455075HCID 59455075, compound

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 1-(4-fluorophenyl)ethanone (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 was 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-52888c7a6065470680ecbbd02aad28b9
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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