Trifluoroacetic acid → 2-(2-Hydroxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 856166Notes

Reaction equation

HRID 856166 reaction equation
FC(F)(F)C(O)=O.COC[O:11][CH2:12][CH2:13][CH:14]1[O:18][C:17]2=[N:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][N:16]2[CH2:15]1>C(Cl)Cl>[OH:11][CH2:12][CH2:13][CH:14]1[O:18][C:17]2=[N:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][N:16]2[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 230815542-(2-Methoxymethoxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 230813022-(2-Hydroxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazoleYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 ml) was added to a solution of 2-(2-methoxymethoxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 25 (0.2 g, 0.822 mmol) in methylene chloride (10 ml) followed by stirring at room temperature overnight. The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1), and crystallized from methanol-diisopropyl ether to afford 2-(2-hydroxyethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (0.11 g, yield 65%) as a light yellow powder.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  3. customcrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-6180e0dcca114e6595b814cf8a8c07a5
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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