Tetrabutylammonium Fluoride → 3-((5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol

HRID 2105080Notes

Reaction equation

HRID 2105080 reaction equation
[Si]([O:8][C:9]1[C:10]([F:49])=[C:11]([CH:17]([C:19]2[N:23]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:22]3[CH:43]=[C:44]([CH3:48])[C:45]([CH3:47])=[CH:46][C:21]=3[N:20]=2)[OH:18])[CH:12]=[C:13]([CH2:15][CH3:16])[CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH3:47][C:45]1[C:44]([CH3:48])=[CH:43][C:22]2[N:23]([C:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]([CH:17]([OH:18])[C:11]3[C:10]([F:49])=[C:9]([OH:8])[CH:14]=[C:13]([CH2:15][CH3:16])[CH:12]=3)=[N:20][C:21]=2[CH:46]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68812924(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)(5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)methanol

Product 1

HCID 688148643-((5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenolYield 35.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 415.2 (115 mg, 0.171 mmol) in 2 mL THF at rt, was added TBAF (1 M in THF, 171 μL, 0.171 mmol). The mixture was stirred at rt for 20 min, then was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (0 to 80% EtOAc/hexanes gradient) to afford 34 mg of 3-((5,6-dimethyl-1-trityl-1H-benzo[d]imidazol-2-yl)(hydroxy)methyl)-5-ethyl-2-fluorophenol as a white solid.

Workup

  1. washwashed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography (0 to 80% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-0bc12ae8c3f84d228559cd4ef7870f0c
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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