HRID1465934

反应详情

EQUATION

反应方程式

HRID 1465934 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

CONDITIONS

反应条件

温度
0 °C

PROCEDURE

实验过程

5-Bromo-3-methyl-thiophene-2-carboxylic acid (example 1.b, 10.0 g, 45.2 mmol) was suspended in 40 mL of thionyl chloride. The mixture was heated at reflux temperature for 1 hour and then cooled to 0° C. with an external ice bath. Cold ethyl alcohol (150 mL) was carefully added, and the solution was heated at reflux temperature for 16 hours. Under reduced pressure, the solution was concentrated to ca. one third of the original volume and then diluted with ethyl acetate and washed successively twice with saturated sodium bicarbonate solution, and once with brine. The organic fractions were dried over anhydrous sodium sulfate and concentrated to 7.9 g of a yellow oil: 1H NMR (CDCl3, 200 MHz): δ=6.87 (s, 1H), 4.34-4.23 (q, 1H, J=7.0 Hz), 2.50 (s, 3H), 1.39-1.32 (t, 3H, J=7.0 Hz).

WORKUP

后处理

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturethe solution was heated
  4. temperatureat reflux temperature for 16 hours
  5. concentrationUnder reduced pressure, the solution was concentrated
  6. additiondiluted with ethyl acetate
  7. washwashed successively twice with saturated sodium bicarbonate solution
  8. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  9. concentrationconcentrated to 7.9 g of a yellow oil