Реакция #351634

Уравнение реакции

(S)-1-amino-2-propanol

(RS)-2-(2-oxoethyl)-6-chloro-1-indanone

water

→

(S)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol

Выход 53.0%

Растворители

toluene

toluene

Условия реакции

Обработка

1. 1
   ДругоеThe cooled reaction mixture
2. 2
   Другоеwas purified by column chromatography on silica gel (ethyl acetate/toluene 1:1)

Методика

A solution of 2.5 g of (RS)-2-(2-oxoethyl)-6-chloro-1-indanone and 100 mg of p-toluenesulfonic acid in 120 ml in anhydrous toluene was heated on a water separator. A solution of 3.6 g of (S)-1-amino-2-propanol in 20 ml of anhydrous toluene was added dropwise to the boiling solution over a period of 5 minutes. Subsequently, the mixture was boiled for 30 minutes, during which the solvent was reduced to a volume of 20 ml. The cooled reaction mixture was purified by column chromatography on silica gel (ethyl acetate/toluene 1:1). 1.56 g (53%) of (S)-1-(7-chloro-1,4-dihydro-indeno[1,2-b]pyrrol-1-yl)-propan-2-ol were obtained as a brown oil which was used directly in the next reaction.

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