反応 #214188

反応方程式

(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

収率 85.0%

反応条件

後処理

1. 1
   workup.ADDITIONUpon addition of the acid
2. 2
   その他a white precipitate formed immediately
3. 3
   抽出extracted three times with 200 ml of hexane
4. 4
   乾燥after which the combined organic phases were dried over sodium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.DISTILLATIONThe pale yellow oily residue was distilled

実験手順

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).

出典