Sodium hydride → HCID 86702160, compound

HRID 1776239Notes

Reaction equation

HRID 1776239 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[O:9]=[S:10]1(=[O:21])[CH2:14][CH2:13][CH2:12][N:11]1[C:15]([CH3:20])([CH3:19])[C:16](=[O:18])[CH3:17]>CS(C)=O>[CH3:17][C:16]1([C:15]([N:11]2[CH2:12][CH2:13][CH2:14][S:10]2(=[O:21])=[O:9])([CH3:20])[CH3:19])[CH2:4][O:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86702161HCID 86702161, compound

Product 1

HCID 86702160HCID 86702160, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of 60% sodium hydride in mineral oil (0.039 g, 1.0 mmol) in anhydrous dimethyl sulfoxide (5 mL), under nitrogen, was added trimethylsulfoxonium iodide (0.214 g, 1.0 mmol). The mixture was stirred at 70° C. for 1 hr and then cooled to room temperature. 3-(1,1-Dioxidoisothiazolidin-2-yl)-3-methylbutan-2-one (0.100 g, 0.5 mmol) was added and the reaction mixture was stirred at room temperature for 16 hrs and then heated at 70° C. for 4 hrs. The mixture was cooled to 0° C. and quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-80% ethyl acetate/hexanes) to afford the product as a thick oil (0.065 g, 61%). 1H NMR (300 MHz, CDCl3) δ 3.52-3.12 (m, 4H), 2.76 (d, 1H, J=4.5 Hz), 2.54 (d, 1H, J=4.5 Hz), 2.42-2.20 (m, 2H), 1.60 (s, 3H), 1.43 (s, 3H), 1.35 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 16 hrs
  3. temperatureheated at 70° C. for 4 hrs
  4. temperatureThe mixture was cooled to 0° C.
  5. customquenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried (anhydrous sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by silica gel chromatography (0-80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-723b74c544da4f60b9540b0bd5d81c1f
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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