Water → 4-(2-Hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one

HRID 1985219Notes

Reaction equation

HRID 1985219 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:23][CH2:24][CH3:25])[C:11](=[O:22])[N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:13]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O.O>C1COCC1>[OH:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:23][CH2:24][CH3:25])[C:11](=[O:22])[N:12]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 688674574-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one

Product 1

HCID 577190494-(2-Hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one (16.79 g, assumed 27.8 mmol) was dissolved in THF (160 mL) and then treated with a 1 M solution of tetrabutylammonium fluoride in THF (55.6 mL, 55.5 mmol) and the reaction stirred at room temperature under N2 for 20 minutes. The reaction was worked up extractively with EtOAc and water and the organic layer dried (MgSO4) and the solvent removed in vacuo to give crude product that was purified by flash chromatography using 3% of MeOH in CH2Cl2 to afford 4.65 g (61%) 4-(2-hydroxy-ethyl)-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one. MS (ES+) Calc'd for C16H23N2O2 (M+1) 275. Found m/z 275 (100%). 1H NMR.

Workup

  1. dry with materialthe organic layer dried (MgSO4)
  2. customthe solvent removed in vacuo
  3. customto give crude product that
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-a3a8c5ebb2ab4f8eb43b988a7b66f379
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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