Tetrabutylammonium Fluoride → HCID 23139272, compound

HRID 1171651Notes

Reaction equation

HRID 1171651 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11]/[C:10]/1=[CH:34]\[C:35]1[O:39][CH:38]=[N:37][CH:36]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[O:39]1[C:35](/[CH:34]=[C:10]2\[CH2:11][N:12]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][CH2:14][CH:9]\2[OH:8])=[CH:36][N:37]=[CH:38]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68766704HCID 68766704, compound

Product 1

HCID 23139272HCID 23139272, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-4-(t-butyldimethylsilyloxy)-3-[(1,3-oxazol-5-yl)methylidene]-1-(triphenylmethyl)piperidine (499 mg) in tetrahydrofuran (8 ml) was added tetrabutylammonium fluoride (483 mg) under ice-cooling, and the resulting mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:7) as the eluent to afford the title compound (254 mg, yield: 65%) as a yellow oil.

Workup

  1. temperaturecooling
  2. washwashed with water and saturated aqueous sodium chloride solution
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-dec7aad1e1594583a2dde1619d5e8399
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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