Reaction #1590375

Reaction equation

potassium tert-butoxide

trimethylphosphonoacetate

4-morpholinoacetophenone

THF

→

3-(4-morpholinophenyl)but-2-enoic acid methyl ester

Yield 69.9%

Solvents

HCl

Conditions

Workup

1. 1
   Otherthe temperature below 25° C
2. 2
   TemperatureThe solution was slowly heated to 60° C. for 36 hours
3. 3
   TemperatureThe solution was cooled to room temperature
4. 4
   Extractionextracted with ethyl acetate (2×100 mL)
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationthe filtrate concentrated to a white solid which
8. 8
   Otherwas recrystallized from hexane/ethyl acetate

Procedure

To a chilled (0° C.) solution of potassium tert-butoxide (1.0 M, 37.1 mL) was dropwise added a solution of trimethylphosphonoacetate, keeping the temperature below 25° C. The solution was then allowed to warm to room temperature and stirred for an additional five minutes, after which a solution of 4-morpholinoacetophenone in THF (20 mL) was added in one portion. The solution was slowly heated to 60° C. for 36 hours. The solution was cooled to room temperature, then diluted with a 1.0N HCl solution (100 mL), and extracted with ethyl acetate (2×100 mL). The organic layers were combined and dried over MgSO4, filtered, and the filtrate concentrated to a white solid which was recrystallized from hexane/ethyl acetate to give 3.33 grams of 3-(4-morpholinophenyl)but-2-enoic acid methyl ester intermediate (69.9% yield).

Source