Reaction #1909818

Reaction equation

pivalic acid amide

1,3-dichloro-2-propanone

sodium hydroxide

→

2-tert-butyl-4-chloromethyloxazole

Yield 51.2%

Conditions

Workup

1. 1
   TemperatureAfter having been cooled with ice
2. 2
   workup.ADDITIONadded
3. 3
   ExtractionThen, the resulting product was extracted with ethyl acetate
4. 4
   Washwashed with water
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   OtherThe residual product was purified through column chromatography (silica gel; ethyl acetate:n-hexane=1:8)

Procedure

25 g of pivalic acid amide and 25 g of 1,3-dichloro-2-propanone were mixed and heated on an oil bath at 135° C. for 2.5 hours. After having been cooled with ice, the mixture was made alkaline with an aqueous solution of sodium hydroxide added thereto. Then, the resulting product was extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through column chromatography (silica gel; ethyl acetate:n-hexane=1:8) to obtain 17.5 g of 2-tert-butyl-4-chloromethyloxazole.

Source