Sodium hydride → HCID 66742678, Verbindung

HRID 45904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45904
[Br:1][C:2]1[S:3][C:4]([CH2:7][OH:8])=[CH:5][N:6]=1.Cl[C:10]1[CH:16]2[CH2:17][CH:13]([CH2:14][CH2:15]2)[C:12](=[O:18])[CH:11]=1.[H-].[Na+]>O1CCCC1>[Br:1][C:2]1[S:3][C:4]([CH2:7][O:8][C:10]2[CH:16]3[CH2:17][CH:13]([CH2:14][CH2:15]3)[C:12](=[O:18])[CH:11]=2)=[CH:5][N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 7213124(2-Bromo-1,3-thiazol-5-yl)methanolHCID 57591516HCID 57591516, Verbindung

Produkt 1

HCID 66742678HCID 66742678, VerbindungAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2-bromothiazol-5-yl)methanol (4.85 g, 25 mmol) and 4-chloro-bicyclo[3.2.1]oct-3-en-2-one (3.92 g, 25 mmol) in anhydrous tetrahydrofuran (100 ml) is added, in small portions, sodium hydride (60% dispersion in oil, 1.00 g, 25 mmol) at 0° C. The reaction mixture is stirred overnight and allowed to warm to room temperature. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-(2-bromothiazol-5-ylmethoxy)bicyclo[3.2.1]oct-3-en-2-one (6.43 g)

Aufarbeitung

  1. additionSilica gel is added to the crude
  2. customreaction mixture
  3. customthe solvent is evaporated under reduced pressure
  4. customthe residue is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-969395d855b04c7fbb15e86f4ffde491
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541594B2

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