Sodium Chloride → HCID 86702133, compound

HRID 1776187Notes

Reaction equation

HRID 1776187 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][S:10]([N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH:18]=[O:19])(=[O:12])=[O:11].[Cl-].[Na+]>O1CCCC1.CS(C)=O>[CH3:9][S:10]([N:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[CH:18]1[CH2:2][O:19]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 55269063HCID 55269063, compound

Product 1

HCID 86702133HCID 86702133, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous dimethylsulfoxide (0.750 mL) was added to trimethylsulfoxonium iodide (0.187 g, 0.85 mmol) and sodium hydride (60% mineral oil dispersion, 0.034 g, 0.85 mmol), and the resulting suspension was stirred for 1 hour. To the stirring solution was added 1-(methylsulfonyl)pyrrolidine-2-carbaldehyde (0.100 g, 0.56 mmol) in anhydrous tetrahydrofuran (1 mL) and the mixture was stirred for 2 hours at room temperature. Saturated aqueous sodium chloride (3 mL) was added, and the mixture was extracted with ethyl acetate (3×30 mL). The combined organics were dried (anhydrous sodium sulfate), filtered, and concentrated under reduced pressure to give a dimethylsulfoxide solution (0.473 g) containing crude product, which was used directly in the next step.

Workup

  1. stirringthe mixture was stirred for 2 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  3. dry with materialThe combined organics were dried (anhydrous sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give a dimethylsulfoxide solution (0.473 g)
  7. additioncontaining crude product, which

Sources & evidence

ORD record
ord-47045138238e4b89ae5701a8bbe8eec6
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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