Water → 2-Bromo-1-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol

HRID 1445769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445769
C1C(=O)N([Br:8])C(=O)C1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[O:17][C:18]([CH3:23])=[C:19]([CH:21]=[CH2:22])[N:20]=2)=[CH:12][CH:11]=1.CCOC(C)=O.[OH2:30]>CS(C)=O>[Br:8][CH2:22][CH:21]([C:19]1[N:20]=[C:16]([C:13]2[CH:12]=[CH:11][C:10]([Br:9])=[CH:15][CH:14]=2)[O:17][C:18]=1[CH3:23])[OH:30]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 222611552-(4-Bromo-phenyl)-5-methyl-4-vinyl-oxazole

Produkt 1

HCID 589514762-Bromo-1-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanolAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Add NBS (1.44 g, 8.08 mmol) to a solution of 2-(4-bromo-phenyl)-5-methyl-4-vinyl-oxazole (1.01 g, 4.02 mmol) in water (0.180 mL) and DMSO (30 mL). After 10 min add water and EtOAc. Separate the layers, extract aqueous material with EtOAc, and wash the crude organic extracts with water. Dry over MgSO4, filter and concentrate. Purify on silica gel eluting with 20% EtOAc/Hexanes to give the title compound (1.08 g, 74%): MS (m/e): 362 (M+1).

Aufarbeitung

  1. customSeparate the layers
  2. extractionextract aqueous material with EtOAc
  3. washwash the crude organic extracts with water
  4. dry with materialDry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify on silica gel eluting with 20% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-8491e4d3783b47c2be8d86ebb8dcafdb
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

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