Tetrabutylammonium Fluoride → HCID 57826340, compound

HRID 1665855Notes

Reaction equation

HRID 1665855 reaction equation
C([Si](C)(C)[O:6][CH:7]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C.O>[OH:6][CH:7]([C:16]1[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 10758614HCID 10758614, compound

Product 1

HCID 57826340HCID 57826340, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-2-pyridin-4-yl-ethanone (0.81 mg, 2.46 mmol) prepared in Step 2 in 5 mL of tetrahydrofuran was added a solution of 1.0 M tetra-n-butyl ammonium fluoride in THF (7.4 mL) and the resulting mixture was stirred for 1 hour. After the reaction was complete, the reaction materials were diluted with 50 mL of ethyl acetate and 50 mL of water to dissolve salts, followed by separation of layers. The obtained organic layer was successively washed twice with 50 mL of a brine solution. The organic layer was dried over magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel column chromatography, to give 68 mg (yield: 13%) of 2-hydroxy-1-phenyl-2-pyridin-4-yl-ethanone of the following formula.

Workup

  1. dissolutionto dissolve salts
  2. customfollowed by separation of layers
  3. washThe obtained organic layer was successively washed twice with 50 mL of a brine solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c9a716b44a14dacbc99256888626cec
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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