Tetrabutylammonium Fluoride → 4-[1-hydroxy-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

HRID 1095305Notes

Reaction equation

HRID 1095305 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH:27]([C:55]1[CH:62]=[CH:61][C:58]([C:59]#[N:60])=[CH:57][CH:56]=1)[CH2:28][O:29][CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:35]=1)(C(C)(C)C)(C)C>O1CCCC1.O>[OH:26][CH:27]([C:55]1[CH:56]=[CH:57][C:58]([C:59]#[N:60])=[CH:61][CH:62]=1)[CH2:28][O:29][CH2:30][C:31]1[N:32]=[CH:33][N:34]([C:36]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:35]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 667816954-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

Product 1

HCID 667821894-[1-hydroxy-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 mmol of tetrabutylammonium fluoride (1M solution in tetrahydrofuran) are added to a solution of 1 mmol of 4-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile in 5 ml of tetrahydrofuran, and the solution is stirred at room temperature for 1 hour. The reaction solution is then diluted with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60 F).

Workup

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. dry with materialThe combined organic phases are dried with sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-03a7493536604a24be3a5f4bd8388e0c
Source dataset
uspto-grants-2012_03
Patent number
US08138176B2

Reaction notes

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