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

HRID 1060249Notes

Reaction equation

HRID 1060249 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-bfb6d5cf150d40dca186ab0913abc78f
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

Loading…