Ethylene Glycol → HCID 178460738, compound

HRID 509539Notes

Reaction equation

HRID 509539 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[CH3:9][CH:10]([SH:12])[CH3:11].C(O)CO.C(=O)([O-])[O-].[K+].[K+]>CC(O)C.[Cu]I>[CH:10]([S:12][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1)([CH3:11])[CH3:9]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 63642-PropanethiolHCID 11430Potassium CarbonateHCID 4595002-Hydroxy-5-iodopyridine

Product 1

HCID 178460738HCID 178460738, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Procedure

5-iodopyridin-2-ol (1 g, 4.525 mmol), propane-2-thiol (689.3 mg, 840.6 μL, 9.050 mmol), ethylene glycol (842.9 mg, 757.3 μL, 13.58 mmol), CuI (172.4 mg, 0.9050 mmol) and potassium carbonate (1.877 g, 13.58 mmol) in IPA (7 mL) were heated under microwave conditions at 120° C. for 2 hours. The mixture was filtered through celite washing with DCM and the filtrate concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, loaded in DCM). The fractions were combined and concentrated in vacuo and the residue redissolved in EtOAc (10 mL) and stirred with 0.5 g of 3-Mercaptopropyl ethyl sulfide Silica for 45 minutes. The silica was removed by filtration and the solvent removed in vacuo to give the sub-title compound as a beige oil which was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. washthrough celite washing with DCM
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by column chromatography (ISCO Companion™, 40 g column, eluting with 0 to 100% EtOAc/Petroleum Ether, loaded in DCM)
  5. concentrationconcentrated in vacuo
  6. dissolutionthe residue redissolved in EtOAc (10 mL)
  7. customThe silica was removed by filtration
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-da8f1eae412f4c1eb92a9e1652953b59
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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