Benzyl Bromide → HCID 67282870, Verbindung

HRID 1187478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1187478
[OH-].[Na+].[OH:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:15])[F:14].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CO>[CH2:18]([O:3][C:4]1[C:9](=[O:10])[CH:8]=[CH:7][N:6]([CH3:11])[C:5]=1[CH:12]([OH:17])[C:13]([F:16])([F:14])[F:15])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 67282261HCID 67282261, Verbindung

Produkt 1

HCID 67282870HCID 67282870, VerbindungAusbeute 31,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of NaOH (1.77 g dissolved in 20 mL, 44.4 mmol) in de-ionized water was added dropwise to a suspension of 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (9.00 g, 40.3 mmol) in methanol (100 mL), and followed by benzyl bromide (5.28 mL, 44.4 mmol) at room temperature. The resulting suspension was refluxed for 3.5 h, and then stirred at RT for overnight. Methanol was removed under vacuum using the rotary evaporator, and the residue was diluted with water and extracted two times with CH2Cl2 (2×100 mL). The combined organic fractions were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to dryness. The residue was purified by flash column chromatography on silica gel using a mixture of methanol and ethyl acetate (10/90, v/v) as eluant. Fractions rich in the product were pooled together and evaporated to dryness to give 4 g of 3-benzyloxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid.

Aufarbeitung

  1. temperatureThe resulting suspension was refluxed for 3.5 h
  2. customMethanol was removed under vacuum
  3. customthe rotary evaporator
  4. additionthe residue was diluted with water
  5. extractionextracted two times with CH2Cl2 (2×100 mL)
  6. washThe combined organic fractions were washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash column chromatography on silica gel using
  11. additiona mixture of methanol and ethyl acetate (10/90
  12. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e11a9904b65d4f3a97efb856dad4a9dd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673943B2

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