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

HRID 1385194Notes

Reaction equation

HRID 1385194 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-65bc07e5a21343ce831b411f55b81294
Source dataset
uspto-grants-2001_07
Patent number
US06262096B1

Reaction notes

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