反応 #888

反応方程式

1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene

KBr

→

2,5-bis(4-Bromophenyl)-3-(p-tolyloxy)furan

溶媒

phosphorus trichloride

反応条件

後処理

1. 1
   温度under reflux for 3-4 hr (TLC followed)
2. 2
   その他The excess PCl3 was removed by distillation
3. 3
   その他the residue was triturated with ice/water (exothermic reaction)
4. 4
   抽出The solution was extracted with dichloromethane (75 ml)
5. 5
   洗浄the dichloromethane layer was washed with saturated sodium bicarbonate solution, water
6. 6
   その他dried (Na2 SO4)
7. 7
   その他The solvent was removed under reduced pressure
8. 8
   その他The residual solid was chromatographed over silica gel
9. 9
   その他An off white crystalline solid was obtained

実験手順

A solution of 5.0 g (0.01 mole) 1-(4-tolyloxy)-1,2-bis-(4-bromobenzoyl)ethylene in 10 ml phosphorus trichloride was heated under reflux for 3-4 hr (TLC followed). The excess PCl3 was removed by distillation and the residue was triturated with ice/water (exothermic reaction). The solution was extracted with dichloromethane (75 ml) and the dichloromethane layer was washed with saturated sodium bicarbonate solution, water, and dried (Na2 SO4). The solvent was removed under reduced pressure. The residual solid was chromatographed over silica gel using ether:hexane (2:8 to 1:1) as eluant. An off white crystalline solid was obtained, 2.78 g (56%), mp 92°-3° C. IR (KBr) 2923, 2851, 1560, 1506, 1467, 1390, 1209, 1072, 1066, 945, 825, 707, 486. 1H NMR (CDCl3 /35° C.) 7.69 (d, 2H, J=8.8), 7.46-7.43 (m, 6H), 7.12 (d, 2H, J=8.3), 7.0 (d, 2H, J=8.3), 6.47 (s, 1H), 2.31 (s, 3H). 13C NMR (CDCl3 /135° C.) 150.8, 150.1, 142.8, 139.3, 133.0, 131.9, 131.7, 130.3, 129.1, 128.6, 125.1, 125.0, 121.8, 120.5, 117.1, 102.7, 20.6. MS m/e 484 (M+).

出典