HRID563940

反应详情

EQUATION

反应方程式

HRID 563940 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

3

PROCEDURE

实验过程

A solution of 40.0 grams (0.243 mol, 1.0 eq) of 2-Chloro-3-oxo-butyric acid ethyl ester in 240 mL formic acid (99%) was stirred at room temperature in a 500 mL round bottom flask equipped with a H2O condenser. To this solution was added 80.0 grams (1.27 mmol, 5.2 eq) of ammonium formate. The solution was then heated to reflux for five hours. After cooling to room temperature, the solution was diluted with water (1 L) and neutralized with Na2CO3. The aqueous solution was then extracted three times with Et2O and the combined organic fractions were dried over MgSO4. After concentration, vacuum distillation (˜10 mmHg, b.p. 53° C.-61° C.) gave a mixture of starting material and 4-Methyl-oxazole-5-carboxylic acid ethyl ester as a colorless oil (21.7 grams). This mixture was dissolved in 100 mL of aqueous sodium hydroxide (2 N) and refluxed for 1 minute. The reaction was then poured onto ice and acidified with concentrated HCl and the known (Sen & Sengupta (1985) Ind. J. Chem. Section B: Org. Chem. Including Med. Chem. 24B(5):535-8) free acid precipitated as a white solid (6.04 grams, 20% overall yield) Mp: 241.4-242.6° C.

WORKUP

后处理

  1. customequipped with a H2O condenser
  2. temperatureThe solution was then heated
  3. temperatureto reflux for five hours
  4. extractionThe aqueous solution was then extracted three times with Et2O
  5. dry with materialthe combined organic fractions were dried over MgSO4
  6. concentrationAfter concentration, vacuum distillation (˜10 mmHg, b.p. 53° C.-61° C.)
  7. customgave
  8. temperaturerefluxed for 1 minute
  9. additionThe reaction was then poured onto ice
  10. custom535-8) free acid precipitated as a white solid (6.04 grams, 20% overall yield) Mp: 241.4-242.6° C.