تفاعل #1071919

معادلة التفاعل

triethylamine

vinyl bromide

2-pentyl-5-(N-methyl-anilinomethylene)cyclopentanone

sodium t-butoxide

→

title compound

المردود 90.1%

2-pentyl-2-vinyl-5-(N-methyl-anilinomethylene)cyclopentanone

المردود 90.1%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىAn oven dried Schlenk tube
2. 2
   أخرىequipped with a rubber septum
3. 3
   أخرىwas purged with argon
4. 4
   أخرىThe septum was removed
5. 5
   أخرىThe tube was capped with the septum
6. 6
   workup.ADDITIONwere added through the septum
7. 7
   أخرىThe septum was removed
8. 8
   أخرىThe tube was capped with the septum
9. 9
   أخرىpurged with argon
10. 10
    workup.ADDITIONAdditional toluene (4 mL) was added
11. 11
    workup.STIRRINGthe mixture was stirred at room temperature for 18 h
12. 12
    أخرىThe mixture was quenched with saturated aqueous ammonium chloride (5 mL)
13. 13
    workup.ADDITIONdiluted with ether (20 mL)
14. 14
    workup.ADDITIONpoured into a separatory funnel
15. 15
    أخرىThe layers were separated
16. 16
    استخلاصthe aqueous layer was extracted with ether (20 mL)
17. 17
    غسيلThe combined organic layers were washed with brine (20 mL)
18. 18
    تجفيفdried over anhydrous magnesium sulfate
19. 19
    ترشيحfiltered
20. 20
    تركيزconcentrated in vacuo
21. 21
    أخرىThe crude material was purified by flash chromatography on silica gel

الإجراء التجريبي

An oven dried Schlenk tube equipped with a rubber septum was purged with argon. The septum was removed, and the tube was charged with tris(dibenzylideneacetone) dipalladium (0) (11.4 mg, 0.013 mmol, 5 mol % Pd) and (+)-2-(dicyclohexylphosphino)2′-(dimethylamino)-1,1′-binaphthyl (13.6 mg, 0.028 mmol 6 mol %). The tube was capped with the septum, purged with argon, and toluene (2 mL) and triethylamine (5 mg, 0.05 mmol) were added through the septum. The mixture was stirred at room temperature for 3 min, then vinyl bromide (1.0 mL 1.0 mmol) was added through septum. The septum was removed and 2-pentyl-5-(N-methyl-anilinomethylene)cyclopentanone (136 mg, 0.5 mmol) and sodium t-butoxide (96 mg, 1.0 mmol) were added. The tube was capped with the septum and purged with argon. Additional toluene (4 mL) was added and the mixture was stirred at room temperature for 18 h. The mixture was quenched with saturated aqueous ammonium chloride (5 mL), diluted with ether (20 mL) and poured into a separatory funnel. The layers were separated and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 134 mg (90%) of the title compound. The ee was determined to be 80% by chiral HPLC analysis.

المصدر