반응 #1459677

반응 방정식

5-(acetylamino)-2-butyl-1-indanone

NaOMe

methyl vinyl ketone

→

5-(acetylamino)-2-butyl-2-(3-oxobutyl)-1-indanone

수율 87.0%

용매

MeOH

MeOH

반응 조건

후처리

1. 1
   기타The mixture was partitioned between EtOAc and saturated aqueous NH4Cl
2. 2
   추출the aqueous phase was back-extracted with EtOAc
3. 3
   세척The combined organics were washed with 5% NaHCO3, water, and brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated under vacuum to an oil (11.8 g)
7. 7
   기타The crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm)
8. 8
   세척eluting with 2:1 hexane-EtOAc

실험 절차

A solution of 5-(acetylamino)-2-butyl-1-indanone (8.8 g, 35.9 mmol) in MeOH (95 mL) was treated with 0.5M NaOMe in MeOH (14.4 mL, 7.2 mmol). The resulting solution was placed under a N2 atmosphere, treated with methyl vinyl ketone (4.5 mL, 54 mmol), and then stirred at room temperature for three days. The mixture was partitioned between EtOAc and saturated aqueous NH4Cl, and the aqueous phase was back-extracted with EtOAc. The combined organics were washed with 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil (11.8 g). The crude product was purified by Biotage flash chromatography on a 75 L silica gel column (7.5×35 cm), eluting with 2:1 hexane-EtOAc, to provide 5-(acetylamino)-2-butyl-2-(3-oxobutyl)-1-indanone (9.8 g, 87%) as a clear oil.

출처