تفاعل #1509650

معادلة التفاعل

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

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthen purged with nitrogen for 15 min
2. 2
   أخرىThe greenish-brown suspension solution was purged with nitrogen for 15 min
3. 3
   ترشيحThe reaction mixture was filtered thru celite
4. 4
   استخلاصthe purple precipitate was extracted with chloroform
5. 5
   استخلاصThe chloroform extract
6. 6
   تركيزwas concentrated
7. 7
   استخلاصthe resulting solid was soxhlet-extracted with hexanes
8. 8
   استخلاصthen extracted with chloroform
9. 9
   أخرىThe solvent was removed
10. 10
    أخرىto afford
11. 11
    أخرىa purple solid (2.1 g, 66% S5 yield)

الإجراء التجريبي

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

المصدر