반응 #55073

반응 방정식

ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropionate

o-chlorocinnamic acid

triethylamine

ethyl chloroformate

→

ethyl 2-{4-[2-(2-chlorocinnamoylamino)-ethyl]-phenoxy}-2-methylpropionate

수율 65.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONTo a mixture of 11.50 g
2. 2
   workup.STIRRINGthe reaction mixture is stirred for a further 2 hours at -10° C.
3. 3
   workup.WAITleft
4. 4
   workup.WAITto stand for a day at ambient temperature
5. 5
   workup.DISTILLATIONThereafter, the tetrahydrofuran is distilled off in a vacuum
6. 6
   추출The methylene chloride phase is extracted with 0.5 N aqueous sodium hydroxide solution
7. 7
   여과filtered
8. 8
   건조dried over anhydrous sodium sulphate
9. 9
   기타evaporated
10. 10
    기타After recrystallization of the residue
11. 11
    workup.ADDITIONfrom a mixture of ligroin and acetone (30:5 v/v)

실험 절차

To a mixture of 11.50 g. (63 mMol) o-chlorocinnamic acid, 200 ml. anhydrous tetrahydrofuran and 6.38 g. (63 mMol) anhydrous triethylamine, there are added dropwise at -15° C., 7.50 g. (69 mMol) ethyl chloroformate. The reaction mixture is then stirred for 15 minutes at -15° C. Subsequently, a solution of 15.80 g. (63 mMol) ethyl 2-[4-(2-aminoethyl)phenoxy]-2-methylpropionate in 50 ml. anhydrous tetrahydrofuran is added dropwise thereto and the reaction mixture is stirred for a further 2 hours at -10° C. and then left to stand for a day at ambient temperature. Thereafter, the tetrahydrofuran is distilled off in a vacuum and the residue is taken up in methylene chloride. The methylene chloride phase is extracted with 0.5 N aqueous sodium hydroxide solution, filtered, dried over anhydrous sodium sulphate and evaporated. After recrystallization of the residue from a mixture of ligroin and acetone (30:5 v/v), there is obtained, in a yield of 65% of theory, ethyl 2-{4-[2-(2-chlorocinnamoylamino)-ethyl]-phenoxy}-2-methylpropionate, which melts at 76° C.

출처