Tetrabutylammonium Fluoride → 1-(4-Hydroxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

HRID 274940Notes

Reaction equation

HRID 274940 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:17]2=[O:30])=[CH:11][C:10]=1[CH2:31][CH2:32][CH3:33])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:17]2=[O:30])=[CH:11][C:10]=1[CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 200891961-(4-Tert-butyldimethylsilyloxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinone

Product 1

HCID 200891871-(4-Hydroxy-3-propylphenylmethyl)-3-carboethoxy-2-benzimidazolinoneYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.334 g (0.71 mmol) of the product of step B in 1 mL of anhydrous THF was added 728 gL (0.73 mmol) of a 1.0 M solution of tetrabutylammonium fluoride in THF and the resulting mixture was stirred at room temperature for 10 minutes. The THF was then removed in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 40% EtOAc-hexane. Combination of the product containing fractions and evaporation in vacuo afforded 0.109 g (43%) of the title compound.

Workup

  1. customThe THF was then removed in vacuo
  2. customthe residue was purified on a silica gel flash chromatography column
  3. washeluted with 40% EtOAc-hexane
  4. additionCombination of the product containing
  5. customfractions and evaporation in vacuo

Sources & evidence

ORD record
ord-e844916eae1f425dab3715b2ed36dddc
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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