反応 #50466

反応方程式

crude product

3-chloro-α-(4-chlorophenyl)benzenepropanoic acid

→

yellow oily solid

5-chloro-2-(4-chlorophenyl)-2,3-dihydro-1H-inden-1-one

溶媒

thionyl chloride

反応条件

後処理

1. 1
   温度heated
2. 2
   温度at reflux for 2 hours
3. 3
   その他Thionyl chloride was removed by concentration at reduced pressure
4. 4
   濃縮the mixture was concentrated several times from carbon tetrachloride
5. 5
   workup.ADDITION24.5 g of aluminum trichloride was then added
6. 6
   workup.ADDITIONwas poured onto a mixture of ice in 1N hydrochloric acid
7. 7
   抽出extracted three times with ether
8. 8
   その他chromatographed on silica gel (10% ethyl acetate/hexane)

実験手順

The crude product from Step A was combined with 50 ml of thionyl chloride and then heated at reflux for 2 hours. Thionyl chloride was removed by concentration at reduced pressure and then the mixture was concentrated several times from carbon tetrachloride. The residue was combined with 200 ml of dichloroethane, cooled under nitrogen to 0° C., and 24.5 g of aluminum trichloride was then added. After stirring overnight the reaction was poured onto a mixture of ice in 1N hydrochloric acid, extracted three times with ether and chromatographed on silica gel (10% ethyl acetate/hexane) to afford 18.6 g of a yellow oily solid. 1H NMR (CDCl3) δ 3.20 (dd, 1H), 3.68 (dd, 1H), 3.90 (dd, 1H), 6.9-7.6 (m), 7.75 (d, 1H) .

出典