2-Methoxyethanol → HCID 59497150, compound

HRID 2046524Notes

Reaction equation

HRID 2046524 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].Cl[C:9]1[C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=[C:11]([CH3:23])[CH:10]=1>C1COCC1>[CH3:3][O:4][CH2:5][CH2:6][O:7][C:9]1[C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=[C:11]([CH3:23])[CH:10]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 59497129HCID 59497129, compound

Product 1

HCID 59497150HCID 59497150, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (60% in mineral oil, 1.75 g, 43.7 mmol) in THF (30 mL) a solution of 2-methoxyethanol (3.30 g, 43.7 mmol) in anhydrous THF (10 mL) was slowly added. The mixture was stirred at room temperature for 20 minutes and a solution of 4-chloro-2-methyl-[1,10]phenanthroline (2.00 g, 8.8 mmol) in anhydrous THF (20 mL) was added. The reaction mixture was refluxed for 18 hours and the solvent was removed in a rotary evaporator. The residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL) and transferred to a separatory funnel. The organic layer was washed with brine (100 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was washed with hexane and purified by flash chromatography (SiO2, MeOH/DCM, 1:30) to afford the pure product as a light yellow solid (1.17 g, 50%).

Workup

  1. additionwas slowly added
  2. temperatureThe reaction mixture was refluxed for 18 hours
  3. customthe solvent was removed in a rotary evaporator
  4. additionThe residue was treated with methylene choride (100 mL) and saturated NaHCO3 (100 mL)
  5. customtransferred to a separatory funnel
  6. washThe organic layer was washed with brine (100 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. washThe residue was washed with hexane
  11. custompurified by flash chromatography (SiO2, MeOH/DCM, 1:30)

Sources & evidence

ORD record
ord-1b6ac90fdbbf4327917fb37dde77d326
Source dataset
uspto-grants-2013_11
Patent number
US08592446B2

Reaction notes

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