Water → HCID 57809818, compound

HRID 400658Notes

Reaction equation

HRID 400658 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[F:9][C:10]([F:29])([F:28])[C:11](=[O:27])[CH2:12][C:13]([CH3:26])([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=1)[CH3:14].O>CS(C)=O>[CH3:26][C:13]([C:15]1[C:23]2[O:22][CH2:21][CH2:20][C:19]=2[CH:18]=[C:17]([S:24][CH3:25])[CH:16]=1)([CH3:14])[CH2:12][C:11]1([C:10]([F:9])([F:28])[F:29])[CH2:2][O:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 57809816HCID 57809816, compound

Product 1

HCID 57809818HCID 57809818, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of trimethylsulfoxonium iodide (1.36 g, 6.1 mmol) in 7.7 mL of anhydrous DMSO was added sodium hydride (60% dispersion in mineral oil, 246 mg). The resulting solution was stirred at room temperature for 30 minutes and was then added dropwise to a solution of 1,1,1-trifluoro-4-methyl-4-(5-methylsulfanyl-2,3-dihydrobenzofuran-7-yl)pentan-2-one (1.63 g, 6.2 mmol) in 6.5 mL of anhydrous DMSO. After 2 hours, 100 mL of water was added and the resulting mixture was extracted with three 100 mL portions of diethyl ether. The combined organic phases were washed twice with water, aqueous saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound, 1.64 g (95% yield) which was used without further purification.

Workup

  1. waitAfter 2 hours
  2. extractionthe resulting mixture was extracted with three 100 mL portions of diethyl ether
  3. washThe combined organic phases were washed twice with water, aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-88ee16741b99497fbf516791ed83c0cb
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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