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

HRID 1360140Notes

Reaction equation

HRID 1360140 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 60F).

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-d2841cffc3a94483b3697e0987866592
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

Loading…