1,3-Dichloroacetone → 2-tert-Butyl-4-(chloromethyl)-1,3-oxazole

HRID 990735Notes

Reaction equation

HRID 990735 reaction equation
[C:1]([NH2:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:8][CH2:9][C:10](=O)[CH2:11]Cl.[OH-].[Na+]>>[C:2]([C:1]1[O:6][CH:11]=[C:10]([CH2:9][Cl:8])[N:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 107931,3-DichloroacetoneHCID 12957TrimethylacetamideHCID 14798Sodium Hydroxide

Product 1

HCID 221695102-tert-Butyl-4-(chloromethyl)-1,3-oxazoleYield 51.2%

Conditions

Temperature
135 °C

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.

Workup

  1. temperatureAfter having been cooled with ice
  2. additionadded
  3. extractionThen, the resulting product was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residual product was purified through column chromatography (silica gel; ethyl acetate:n-hexane=1:8)

Sources & evidence

ORD record
ord-120e4bb1a1d540faaba9e4e76c9da5bf
Source dataset
uspto-grants-2002_10
Patent number
US06462049B1

Reaction notes

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