Tetrabutylammonium Fluoride → HCID 68813439, compound

HRID 2105088Notes

Reaction equation

HRID 2105088 reaction equation
[Si]([O:8][C:9]1[C:10]([F:49])=[C:11]([CH:17]([C:19]2[N:20]([C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([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)[CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=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>[CH2:15]([C:13]1[CH:12]=[C:11]([CH:17]([OH:18])[C:19]2[N:20]([C:30]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)[C:10]([F:49])=[C:9]([OH:8])[CH:14]=1)[CH3:16]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69125238(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl) (4-phenyl-1-trityl-1H-imidazol-2-yl)methanol

Product 1

HCID 68813439HCID 68813439, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of intermediate 448.1 (1.74 g, 2.60 mmol) in 10 mL THF at rt, was added TBAF (1M in THF, 2.60 mL, 2.60 mmol). The mixture was stirred at rt for 30 min, then was diluted with EtOAc, washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The crude product was triturated with hexanes (10 mL) to afford after filtration 1.32 g of intermediate 448.2 as a white solid. LCMS (2 min gradient) RT=1.81 min, 555.3 (M+H)+.

Workup

  1. washwashed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was triturated with hexanes (10 mL)
  5. customto afford
  6. filtrationafter filtration 1.32 g of intermediate 448.2 as a white solid
  7. customLCMS (2 min gradient) RT=1.81 min, 555.3 (M+H)+

Sources & evidence

ORD record
ord-eb3911a35c4b4027bdb0b1ac75f158ee
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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