Ethanol → Imidazole,2-nitro-1-(3-methoxy-2-fluoro)propyl-

HRID 1651303Notes

Reaction equation

HRID 1651303 reaction equation
O[CH:2]([CH2:12][O:13][CH3:14])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].CCN(S(F)(F)[F:21])CC.C(O)C>O1CCOCC1>[F:21][CH:2]([CH2:12][O:13][CH3:14])[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 261051-Methoxy-3-(2-nitro-1H-imidazol-1-yl)propan-2-olHCID 123472(Diethylamino)sulfur trifluoride2×

Product 1

HCID 14458239Imidazole,2-nitro-1-(3-methoxy-2-fluoro)propyl-Yield 52%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 914 mg (4.54 mmol) of 1-(2'-hydroxy-3'-methoxypropyl)-2-nitroimidazole in 5.0 ml of dry dioxane, 1.00 g (6.20 mmol) of DAST was dropwise added with cooling by ice and then reacted for 2 hours at room temperature with stirring. After reaction, to the solution, 5.0 ml of ethanol was added to decompose excess DAST. The solution was then concentrated and subjected to isolation and purification by silica gel column chromatography to give 480 mg of 1-(2-'-fluoro-3'-methoxypropyl)-2-nitroimidazole.

Workup

  1. temperaturewith cooling by ice
  2. customreacted for 2 hours at room temperature
  3. customAfter reaction
  4. concentrationThe solution was then concentrated
  5. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-7e00863cc65f4446bebd24839e142b43
Source dataset
uspto-grants-1990_05
Patent number
US04927941

Reaction notes

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