Imidazole → HCID 22620101, compound

HRID 840600Notes

Reaction equation

HRID 840600 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-4d48cbbfe28b4a018d6d53a2b5c54fb5
Source dataset
uspto-grants-2002_04
Patent number
US06369074B1

Reaction notes

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