Tetrabutylammonium Fluoride → HCID 68817342, compound

HRID 2104981Notes

Reaction equation

HRID 2104981 reaction equation
[Si]([O:8][C:9]1[C:10]([F:58])=[C:11]([N:18]([CH2:27][C:28]2[N:29]([C:39]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:32]=2)[C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[CH2:16]([O:15][C:13]1[CH:14]=[C:9]([OH:8])[C:10]([F:58])=[C:11]([N:18]([CH2:27][C:28]2[N:29]([C:39]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:30]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:32]=2)[C:19]2[CH:20]=[CH:21][C:22]([C:23]#[N:24])=[CH:25][CH:26]=2)[CH:12]=1)[CH3:17]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68812573HCID 68812573, compound

Product 1

HCID 68817342HCID 68817342, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 113.2 (620 mg, 0.790 mmol) in 5 mL THF at rt, was added TBAF (1M, 0.79 mL, 0.790 mmol). The mixture was stirred at rt for 1 h, then was diluted with EtOAc. The organic phase was washed with sat. NH4Cl (2×), H2O (2×) and brine, dried (Na2SO) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes, gradient) to afford 530 mg (100%) of Intermediate 113.3 as a colorless solid.

Workup

  1. washThe organic phase was washed with sat. NH4Cl (2×), H2O (2×) and brine
  2. dry with materialdried (Na2SO)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-7afa5dea51114605a5a712e99a3f1580
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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