Dimethyl Sulfoxide → HCID 59455075, compound

HRID 1481390Notes

Reaction equation

HRID 1481390 reaction equation
CS(C)=O.[H-].[Na+].[I-].C([S+](CC)CC)C.[F:15][C:16]1[CH:21]=[CH:20][C:19](C(=O)C)=[CH:18][CH:17]=1.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:27]2([CH3:26])[CH:29]([CH3:25])[O:28]2)=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8028Tetrahydrofuran2×HCID 98284'-FluoroacetophenoneHCID 24758Sodium hydrideHCID 74589Triethylsulfanium iodide

Product 1

HCID 59455075HCID 59455075, compound

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. Triethylsulfonium iodide (1 equiv.) was added and stirred for 10 min. after which the solution of 1-(4-fluorophenyl)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-5128732c6bf0441cb53690aa75630836
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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