Реакция #76299

Уравнение реакции

hydrogen chloride

[4-(cyclopropylcarbonyl)phenyl]methyl-propanedioic acid, diethyl ester

→

title compound

Выход 59.0%

[4-(4-chloro-1-oxobutyl)phenyl]methyl-propanedioic acid, diethyl ester

Выход 59.0%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ТемператураHeat the solution
2. 2
   Температураto reflux
3. 3
   Другоеbubble nitrogen through the solution for 1 hour
4. 4
   СушкаDry the organic phase over anhydrous magnesium sulfate
5. 5
   Концентрированиеconcentrate
6. 6
   workup.DISSOLUTIONDissolve the crude product in ethanol (50 mL)
7. 7
   Другоеbubble hydrogen chloride gas through the solution for 10 minutes
8. 8
   ТемператураHeat the solution
9. 9
   Температураto reflux
10. 10
    Концентрированиеconcentrate the solution
11. 11
    СушкаDry the organic phase over anhydrous magnesium sulfate
12. 12
    Концентрированиеconcentrate
13. 13
    ДругоеPurify by flash chromatography (150 g silica gel, 20% ethyl acetate/heptane as eluent)

Методика

Bubble hydrogen chloride gas through a solution of [4-(cyclopropylcarbonyl)phenyl]methyl-propanedioic acid, diethyl ester (570 mg, 2.0 mmol) in ethanol (4 mL) for 5 minutes. Heat the solution to reflux. After 18 hours, cool the solution to room temperature and bubble nitrogen through the solution for 1 hour. Add ethyl acetate and water to the residue. Dry the organic phase over anhydrous magnesium sulfate and concentrate. Dissolve the crude product in ethanol (50 mL) and bubble hydrogen chloride gas through the solution for 10 minutes. Heat the solution to reflux. After stirring 2 days, concentrate the solution. Add water and ethyl acetate to the residue. Dry the organic phase over anhydrous magnesium sulfate and concentrate. Purify by flash chromatography (150 g silica gel, 20% ethyl acetate/heptane as eluent) to give the title compound (409 mg, 59%).

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