Ammonium Chloride → 1-(2-Bromo-thiazol-5-yl)-propan-1-ol

HRID 559687

Reaktionsgleichung

Reaktionsgleichung von HRID 559687
[Br:1][C:2]1[S:3][C:4]([CH:7]=[O:8])=[CH:5][N:6]=1.[CH2:9]([Mg]Br)[CH3:10].[Cl-].[NH4+]>C1COCC1.C(OCC)C.CCOC(C)=O>[Br:1][C:2]1[S:3][C:4]([CH:7]([OH:8])[CH2:9][CH3:10])=[CH:5][N:6]=1

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 584433781-(2-Bromo-thiazol-5-yl)-propan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-thiazole-5-carbaldehyde (1.00 g, 5.21 mmol) in THF (10 mL) was added a 3 M solution of ethylmagnesium bromide (5.00 mL, 15.0 mmol) in diethyl ether. The mixture was stirred for 18 hours. The reaction was poured into saturated aqueous ammonium chloride (100 mL) containing crushed ice and diluted with EtOAc (100 mL). The organic phase was separated, washed with saturated aqueous sodium bicarbonate solution (100 mL), dried over sodium sulfate, filtered and concentrated. The compound was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes provided 1-(2-bromo-thiazol-5-yl)-propan-1-ol.

Aufarbeitung

  1. additioncontaining
  2. customcrushed ice
  3. customThe organic phase was separated
  4. washwashed with saturated aqueous sodium bicarbonate solution (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound was purified by silica gel chromatography
  9. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-20fafa3892d94be4b24ff1acf6e49953
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063065B2

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