Imidazole → HCID 22620101, compound

HRID 1459591Notes

Reaction equation

HRID 1459591 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>O1CCCC1.[Cu]>[NH:15]1[CH:19]=[CH:18][N:17]=[C:16]1[C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:7]=1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 22620058HCID 22620058, compound

Product 1

HCID 22620101HCID 22620101, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

In a Pyrex high pressure reaction tube, a solution of the preceding dioxolane (200 mg, 0.66 mmol), 140 mg (2.06 mmol) of imidazole and 90 mg (1.4 mmol) of copper powder in 1 mL of anhydrous tetrahydrofuran (THF) was stirred until homogeneous. The solvent was then evaporated under nitrogen, and the tube was sealed and heated in an oil bath at 140° C. for 16 hours. After cooling, the residue was dissolved in 20 mL of THF, filtered through a pad of diatomaceous earth and concentrated in vacuo to an oil. Chromatography on silica gel (100% ethyl acetate (EtOAc)) gave 60 mg of 2-(5-(2-imidazolyl)-2-methoxyphenyl)-1,3-dioxolane as a yellow oil.

Workup

  1. customIn a Pyrex high pressure reaction tube
  2. customThe solvent was then evaporated under nitrogen
  3. customthe tube was sealed
  4. temperatureAfter cooling
  5. dissolutionthe residue was dissolved in 20 mL of THF
  6. filtrationfiltered through a pad of diatomaceous earth
  7. concentrationconcentrated in vacuo to an oil

Sources & evidence

ORD record
ord-b8831f45f7994fa6aee30fff6a91b1d4
Source dataset
uspto-grants-1998_12
Patent number
US05854262

Reaction notes

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