Ammonium Chloride → 1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol

HRID 490716

Reaktionsgleichung

Reaktionsgleichung von HRID 490716
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:16]=[O:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.[CH3:18][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:16]([OH:17])[CH3:18])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 858606262-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehydeHCID 178418573HCID 178418573, Verbindung2×

Produkt 1

HCID 587656641-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanolAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-(4-bromo-phenyl)-4-isopropyl-oxazole-5-carbaldehyde (14.4 g, 84.9 mmol) in THF (300 mL) is cooled to −78° C. and treated dropwise with methyl magnesium bromide (25 mL, 75 mmol, 3M Et2O). After 1 h, more methyl magnesium bromide (12 mL, 36 mmol) is added. The reaction mixture is stirred 1.5 h, and saturated NH4Cl solution (10 ml) is added dropwise. The mixture is partitioned between saturated NH4Cl solution (10 ml), 1N HCl (25 mL), and Et2O (300 mL). The organic layer is washed with brine (150 mL), dried (Na2SO4), and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (9:1 to 5:1) to give an offwhite solid (9.5 g, 63%).

Aufarbeitung

  1. customThe mixture is partitioned between saturated NH4Cl solution (10 ml), 1N HCl (25 mL), and Et2O (300 mL)
  2. washThe organic layer is washed with brine (150 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-82dfdae890274655b6ab6e259470ed3a
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528160B2

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