Tetrabutylammonium Fluoride → 2-(4-Fluorobenzoyl)-3-hydroxypyridine

HRID 986975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986975
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[C:13]([O:14][Si](CCCC)(CCCC)CCCC)=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 229879642-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

Produkt 1

HCID 229879782-(4-Fluorobenzoyl)-3-hydroxypyridineAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-(4-fluorobenzoyl)-3-(tributylsilyloxy)pyridine (3.75 g, 11.3 mmol) in tetrahydrofuran (17 ml) was cooled to 0° C. and tetrabutylammonium fluoride (17 ml, 1.0 M in tetrahydrofuran) was added. After 2 h, the reaction mixture was diluted with ethyl acetate. The organic layer was separated, washed with sodium bicarbonate and brine, and dried over sodium sulfate. The organics were removed in vacuo and the residue was purified on a silica gel column using ethyl acetate-hexane (2:8) as the eluant to give 2-(4-fluorobenzoyl)-3-hydroxypyridine (2.2 g).

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customThe organics were removed in vacuo
  5. customthe residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-81604a4f0516495ca88ab980d1cbf15d
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630485B2

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