Reacción #1256714

Ecuación de reacción

11

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

12

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

PPh3

→

title compound

Rendimiento 91.2%

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

Rendimiento 91.2%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevacuated
2. 2
   workup.ADDITIONNext, dry Et3N (10 mL) was added under an N2 flow
3. 3
   Otrothe mixture was degassed by 3 freeze-thaw cycles
4. 4
   TemperaturaThe reaction mixture was then cooled to room temperature
5. 5
   workup.ADDITIONdiluted with methylene chloride (50 mL)
6. 6
   Filtraciónfiltered through a thin pad of silica gel
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otroto afford a red solid
9. 9
   OtroThe crude product was purified by flash chromatography on silica gel
10. 10
    Lavadoeluting with 3:1 hexane

Procedimiento

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.

Fuente