Sodium hydride → HCID 67966894, compound

HRID 527592Notes

Reaction equation

HRID 527592 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH3:9][C:10]1[C:11](=[O:24])[O:12][C:13]2[C:18]([CH:19]=1)=[C:17]([O:20][CH2:21][O:22][CH3:23])[CH:16]=[CH:15][CH:14]=2.[NH4+].[Cl-]>CS(C)=O>[CH3:9][C:10]12[CH2:2][CH:19]1[C:18]1[C:17]([O:20][CH2:21][O:22][CH3:23])=[CH:16][CH:15]=[CH:14][C:13]=1[O:12][C:11]2=[O:24]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86698434HCID 86698434, compound2×

Product 1

HCID 67966894HCID 67966894, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of trimethylsulfoxonium iodide (4.52 g, 20.55 mmol) in dry dimethyl sulfoxide (50 ml) stirred under nitrogen at room temperature was added neat sodium hydride (60%, 0.822 g, 20.55 mmol). The reaction mixture was stirred at room temperature for 1 hour before adding 3-methyl-5-{[(methyloxy)methyl]oxy}-2H-chromen-2-one (Intermediate 113, 1.81 g) dissolved into 15 ml of DMSO. The reaction mixture turned yellow and was heated and stirred at 100° C. for 4 h. The reaction was then worked up by the addition of a saturated solution of NH4Cl and extracted with diethyl ether, washed with brine, dried over sodium sulphate, filtered and concentrated under vacuum. The residue obtained was purified by silica gel chromatography (Biotage system, with a gradient from pure cyclohexane to cyclohexane/ethyl acetate 5/1) to give the title compound as a white solid (360 mg).

Workup

  1. temperaturewas heated
  2. stirringstirred at 100° C. for 4 h
  3. extractionextracted with diethyl ether
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography (Biotage system

Sources & evidence

ORD record
ord-e6489e6f80ec4c6786a70720e728f653
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…