Tetrabutylammonium Fluoride → 4-(Pyrimidin-2-ylmethyl)phenol

HRID 2075223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075223
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:39]=[CH:38][C:30]([CH2:31][C:32]2[N:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1.O>[N:33]1[CH:34]=[CH:35][CH:36]=[N:37][C:32]=1[CH2:31][C:30]1[CH:38]=[CH:39][C:27]([OH:26])=[CH:28][CH:29]=1

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 584153612-(4-(tert-Butyldimethylsilyloxy)benzyl)pyrimidine

Produkt 1

HCID 227684204-(Pyrimidin-2-ylmethyl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (1.68 mL, 1.68 mmol, 1M in THF) was added to a solution of 2-(4-(tert-butyldimethylsilyloxy)benzyl)pyrimidine (0.50 g, 1.68 mmol) in THF (5 mL) at 0° C. The mixture was stirred for 30 min, diluted with water, and extracted with DCM three times. The combined organic extracts were dried over MgSO4, concentrated in vacuo, and purified by column chromatography to give 4-(pyrimidin-2-ylmethyl)phenol as an oil. MS (ESI) m/z: Calculated: 186.1; Observed: 187.3 (M++1).

Aufarbeitung

  1. extractionextracted with DCM three times
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b1c2d85c5e954c369f9b35be8228a736
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919519B2

Notizen zur Reaktion

Wird geladen…