反应 #1509650

反应方程式

2-(2-(2-bromo-5-(trimethylstannyl)thiophen-3-yl)ethyl)-4,5-dihydro-4,4-dimethyloxazol

triphenylphosphine

→

3-(2-(4,5-dihydro-4,4 dimethyl-2-oxazolyl)ethyl)thiophene

溶剂

DMF

反应条件

后处理

1. 1
   其他then purged with nitrogen for 15 min
2. 2
   其他The greenish-brown suspension solution was purged with nitrogen for 15 min
3. 3
   过滤The reaction mixture was filtered thru celite
4. 4
   萃取the purple precipitate was extracted with chloroform
5. 5
   萃取The chloroform extract
6. 6
   浓缩was concentrated
7. 7
   萃取the resulting solid was soxhlet-extracted with hexanes
8. 8
   萃取then extracted with chloroform
9. 9
   其他The solvent was removed
10. 10
    其他to afford
11. 11
    其他a purple solid (2.1 g, 66% S5 yield)

实验过程

2-(2-(2-bromo-5-(trimethylstannyl)thiophen-3-yl)ethyl)-4,5-dihydro-4,4-dimethyloxazol (7.0 g, 15.5 mmol) was weighed in 100 mL Schlenk flask followed by the addition of 30 mL dry DMF then purged with nitrogen for 15 min. To this mixture, copper (II) oxide (1.24 g, 15.5 mmol, 1 eq.), triphenylphosphine (814 mg, 0.031 mmol, 0.20 eq.) and bis(dibenzylidene acetone)palladium(0) (446 mg, 0.776 mmol, 0.05 eq) was added all at once. The greenish-brown suspension solution was purged with nitrogen for 15 min then heated to 100° C. and stirred for 18 hrs under argon atmosphere. The reaction mixture was filtered thru celite and the purple precipitate was extracted with chloroform. The chloroform extract was concentrated and the resulting solid was soxhlet-extracted with hexanes then extracted with chloroform. The solvent was removed to afford a purple solid (2.1 g, 66% S5 yield). 1H NMR (300 MHz, CDCl3): δ=7.06 (s, 1H), 3.94 (s, 2H), 3.14 (d, 2H), 2.66 (d, 2H), 1.28 (s, 6H); 13C NMR (75 MHz, CDCl3): δ=166.7, 138.4, 134.4, 132.4, 129.8, 80.0, 68.0, 29.6, 29.2, 26.4. CDCl3

来源