Chloroacetone → 2-(3-Methoxyphenyl)-4-methyloxazole

HRID 2200561Notes

Reaction equation

HRID 2200561 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[O:7].Cl[CH2:13][C:14](=O)[CH3:15]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[O:7][CH:13]=[C:14]([CH3:15])[N:8]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 984873-Methoxybenzamide

Product 1

HCID 686696072-(3-Methoxyphenyl)-4-methyloxazoleYield 64.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-methoxybenzamide (1.5 g, 9.9 mmol) in toluene (15 mL) was added 1-chloropropan-2-one (1.37 g, 14.9 mmol), and the mixture was stirred at reflux for 16 h. The mixture was cooled and concentrated to give crude product, which was purified via silica gel chromatography eluted with ethyl acetate/petroleum ether (1:5) to give 2-(3-methoxyphenyl)-4-methyloxazole (1.21 g, 64.6% yield) as yellow syrup. LCMS MH+ 190.

Workup

  1. temperatureat reflux for 16 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customwas purified via silica gel chromatography
  6. washeluted with ethyl acetate/petroleum ether (1:5)

Sources & evidence

ORD record
ord-c0aa7f704c2d47d6a84a1096d20c02a0
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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