반응 #214188

반응 방정식

(R)-3-methyl-1-trichloromethylbut-2-en-1-yl (S)-3-[N-(1-(1-naphthyl)ethyl)amino]but-2-enoate

hydrochloric acid

tetrahydrofuran

→

(R)-1-trichloromethyl-3-methyl-2-butenyl acetoacetate

수율 85.0%

반응 조건

후처리

1. 1
   workup.ADDITIONUpon addition of the acid
2. 2
   기타a white precipitate formed immediately
3. 3
   추출extracted three times with 200 ml of hexane
4. 4
   건조after which the combined organic phases were dried over sodium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.DISTILLATIONThe pale yellow oily residue was distilled

실험 절차

To a solution of (R)-3-methyl-1-trichloromethylbut-2-en-1-yl (S)-3-[N-(1-(1-naphthyl)ethyl)amino]but-2-enoate (10 g, 0.023 mole) in tetrahydrofuran (200 ml) at room temperature was added, in one portion, 0.5 N aqueous hydrochloric acid (250 ml, 0.125 mole). Upon addition of the acid, a white precipitate formed immediately, then slowly disappeared. The mixture was stirred at room temperature for a total of 62 hours and then extracted three times with 200 ml of hexane, after which the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The pale yellow oily residue was distilled to yield (R)-1-trichloromethyl-3-methyl-2-butenyl acetoacetate (5.57 g, 85% yield); bp, 90°-92° C. (0.05 mmHg); [α]D25 =+13.00° (CHCl3).

출처