Tetrahydrofuran → 1-Benzyl-4-hydroxy-1,3-dihydro-benzoimidazol-2-one

HRID 730562Notes

Reaction equation

HRID 730562 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([O:17]CC3C=CC=CC=3)[C:11]=2[NH:10][C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=2[NH:10][C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 578350031-Benzyl-4-benzyloxy-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 578349841-Benzyl-4-hydroxy-1,3-dihydro-benzoimidazol-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-4-benzyloxy-1,3-dihydro-benzoimidazol-2-one (0.875 g, 2.64 mmol) in 100 ml of 1:1 ethyl acetate:THF was added palladium hydroxide (0.270 mg, 1.923 mmol). The reaction mixture was purged with hydrogen gas at 1 atm., allowed to stir at room temperature for 2 hours, and then filtered through celite. The filtrate was concentrated in vacuo to give 640 mg (2.64 mmol. quantitative) of 1-benzyl-4-hydroxy-1,3-dihydro-benzoimidazol-2-one as a white solid. MS: 241 (M+H)+.

Workup

  1. customThe reaction mixture was purged with hydrogen gas at 1 atm.
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6fefe272a6fe4268b1f9c2c5546b344f
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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