Chloroacetonitrile → 5-tert-Butyl-2-(chloromethyl)-1,3-oxazole

HRID 1060249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1060249
B(F)(F)F.CCOCC.[N+:10](=[CH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[N-].C(=O)(O)[O-].[Na+].[Cl:24][CH2:25][C:26]#N>>[Cl:24][CH2:25][C:26]1[O:18][C:13]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][N:10]=1

Komponenten

5

Edukt 4

HCID 7856Chloroacetonitrile2×HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 217927841-Diazonio-3,3-dimethylbut-1-en-2-olate

Produkt 1

HCID 129689745-tert-Butyl-2-(chloromethyl)-1,3-oxazole

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2 mL (2.3 g, 16 mmol) of boron trifluoride etherate in 20 mL of chloroacetonitrile at 0° C. was added a solution of 1.33 g (10 mmol) of 1-diazo-3,3-dimethyl-2-butanone in 5 mL of chloroacetonitrile dropwise. The resulting solution was stirred at 0° C. for 0.5 h. The reaction mixture was added to saturated aqueous sodium bicarbonate solution to neutralize the acid and the product was extracted three times with dichloromethane. The combined extracts was dried (sodium sulfate), concentrated and purified by flash column chromatography (Merck silica, 25×200 mm, dichloromethane) to give 1.1 g of 2-(chloromethyl)-5-t-butyloxazole as a yellow liquid (6.4 mmol, 64% overall from the acid chloride).

Aufarbeitung

  1. extractionthe product was extracted three times with dichloromethane
  2. dry with materialThe combined extracts was dried (sodium sulfate)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (Merck silica, 25×200 mm, dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-bfb6d5cf150d40dca186ab0913abc78f
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521759B2

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