Réaction #1256714

Équation de réaction

11

4-(4-iodo-2,6-dimethyl-phenyl)-3,5-dimethyl-pyridine

12

2,6-di-tert-butyl-4-vinyl-phenol

PPh3

→

title compound

Rendement 91.2%

2,6-di-tert-butyl-4-{2-[4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenol

Rendement 91.2%

Conditions de réaction

Traitement

1. 1
   Autreevacuated
2. 2
   workup.ADDITIONNext, dry Et3N (10 mL) was added under an N2 flow
3. 3
   Autrethe mixture was degassed by 3 freeze-thaw cycles
4. 4
   TempératureThe reaction mixture was then cooled to room temperature
5. 5
   workup.ADDITIONdiluted with methylene chloride (50 mL)
6. 6
   Filtrationfiltered through a thin pad of silica gel
7. 7
   Concentrationconcentrated in vacuo
8. 8
   Autreto afford a red solid
9. 9
   AutreThe crude product was purified by flash chromatography on silica gel
10. 10
    Lavageeluting with 3:1 hexane

Mode opératoire

A flame-dried sealable Schlenk tube was charged with 11 (1.69 g, 5.0 mmol), 12 (2.32 g, 10.0 mmol), Pd(OAc)2 (112 mg, 0.50 mmol), and PPh3 (131 mg, 0.50 mmol), evacuated, and then backfilled with N2. Next, dry Et3N (10 mL) was added under an N2 flow. The Schlenk tube was next sealed, the mixture was degassed by 3 freeze-thaw cycles, and backfilled with N2. The Schlenk tube was then wrapped with aluminum foil and stirred at 100° C. for 36 h. The reaction mixture was then cooled to room temperature, diluted with methylene chloride (50 mL), filtered through a thin pad of silica gel, and concentrated in vacuo to afford a red solid. The crude product was purified by flash chromatography on silica gel, eluting with 3:1 hexane: ethyl acetate to give the title compound 2.01 g (91.2%) as a colorless solid: mp 234-235° C.; 1H NMR (400 MHz, CDCl3): δ 8.402 (s, 2H), 7.371 (s, 2H), 7.307 (s, 2H), 7.133 (d, 1H, J=16.4 Hz), 6.936 (d, 1H, J=16.0 Hz), 5.331 (s, 1H), 1.951 (s, 6H), 1.911 (s, 6H), 1.499 (s, 18H); 13C NMR (100 MHz, CDCl3): δ 153.971, 148.630, 148.502, 137.347, 136.301, 135.928, 134.817, 131.251, 129.595, 128.876, 125.837, 125.709, 123.598, 34.638, 30.534, 19.997, 16.822; HRMS (EI): m/z 441.3023 [M+]; calcd, 441.3032; Anal. Calcd. for C31H39NO·H2O: C, 81.00; H, 8.99; N, 3.05. Found; C, 81.01; H, 8.64; N, 3.02.

Source