تفاعل #42752

معادلة التفاعل

benzophenone imine

trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester

cesium carbonate

racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

desired compound

7-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

المذيبات

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGto stir at room temperature for an additional 24 hours
2. 2
   استخلاصextracted with ethyl acetate (3×300 ml)
3. 3
   غسيلwashed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىpurified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane)

الإجراء التجريبي

A mixture of trifluoromethanesulfonic acid 3-(4-chlorophenyl)-2-isopropyl-4-oxo-4H-chromen-7-yl ester (6.96 g, 15.6 mmol), palladium acetate (0.35 g, 1.56 mmol), cesium carbonate (12.7 g, 38.9 mmol) and racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 0.97 g, 1.56 mmol) in anhydrous tetrahydrofuran (230 ml) under an atmosphere of nitrogen is treated with benzophenone imine (3.66 g, 20.2 mmol) and allowed to stir at 80° C. for 22 hours. After allowing the resultant mixture to stir at room temperature for an additional 24 hours, it is diluted with water (300 ml) and extracted with ethyl acetate (3×300 ml). The organic extracts are combined, washed with brine, dried (MgSO4), filtered, concentrated in vacuo and purified by flash chromatography over silica gel (10% ethyl acetate/cyclohexane) to afford the desired compound as a dark yellow solid.

المصدر