1,3-Dichloroacetone → 4-Chloromethyl-2-propyloxazole

HRID 4398

Reaction equation

HRID 4398 reaction equation
[C:1]([NH2:6])(=[O:5])[CH2:2][CH2:3][CH3:4].[Cl:7][CH2:8][C:9]([CH2:11]Cl)=O.C(=O)(O)[O-].[Na+]>O>[Cl:7][CH2:8][C:9]1[N:6]=[C:1]([CH2:2][CH2:3][CH3:4])[O:5][CH:11]=1

Participants

5

Reactant 3

HCID 107931,3-DichloroacetoneHCID 10927ButyramideHCID 516892Sodium Bicarbonate

Product 1

HCID 201524274-Chloromethyl-2-propyloxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of butyramide (19.88 g) and 1.3-dichloroacetone (24.14 g) was heated at 130° C. for 1.5 hours. After cooling, the mixture was diluted with water, neutralized with aqueous sodium bicarbonate solution and extracted with ethyl ether. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel with acetone-hexane (1:9) to yield 4-chloromethyl-2-propyloxazole as an oil (10.70 g 35.3%). NMR (CDCl3)δ: 0.97 (3H, t, J=7.5 Hz), 1.79 (2H, sext, J=7.5 Hz), 2.72 (2H, t, J=7.5 Hz), 4.47 (2H, s), 7.53 (1H, s).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel with acetone-hexane (1:9)

Sources & evidence

ORD record
ord-7d658abe348645fab4f8f7ddde1e6c72
Source dataset
uspto-grants-1988_02
Patent number
US04725610

Linked notes

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