反応 #4085

反応方程式

sulfuric acid

diisobutylaluminum hydride

2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile

potassium hydroxide

tartaric acid

→

2-[3-[(Phenylethyl)methylamino]-propyl]-2-isopropylphenylacetaldehyde

溶媒

hexane

diethyl ether

反応条件

後処理

1. 1
   その他the ether phase was separated off
2. 2
   洗浄washed several times with sodium chloride solution
3. 3
   乾燥After the ether phase had been dried over sodium sulfate
4. 4
   workup.DISTILLATIONthe ether was distilled off
5. 5
   workup.DISSOLUTIONthe remaining oily residue was dissolved in 300 ml of ethyl acetate
6. 6
   workup.ADDITIONhydrochloric acid in isopropanol was added
7. 7
   workup.WAITThe mixture was left
8. 8
   workup.WAITto stand overnight
9. 9
   ろ過after which the precipitated hydrochloride was filtered off under suction

実験手順

180 ml of a 1M solution of diisobutylaluminum hydride in hexane were added dropwise, at -5° C., to a solution of 33.4 g (0.1 mole) of 2-[3-[(phenylethyl)-methylamino]-propyl]-isopropylphenylacetonitrile in 400 ml of diethyl ether. The mixture was stirred for 1.5 hours, after which 500 ml of 10% strength sulfuric acid were added. 30 g of tartaric acid were introduced, the mixture was rendered alkaline with concentrated potassium hydroxide solution, and the ether phase was separated off and washed several times with sodium chloride solution. After the ether phase had been dried over sodium sulfate, the ether was distilled off, the remaining oily residue was dissolved in 300 ml of ethyl acetate, and hydrochloric acid in isopropanol was added. The mixture was left to stand overnight, after which the precipitated hydrochloride was filtered off under suction.

出典