반응 #172179

반응 방정식

Tri(tert-butyl) phosphine

4-bromo-N,N-bis(4-methoxyphenyl)aniline

4-(3-(tert-butyldimethylsilyloxy)propoxy)-N-(4-methoxyphenyl)aniline

sodium tert-butoxide

→

N1-(4-(3-(tert-butyldimethylsilyloxy)propoxy)phenyl)-N1,N4,N4-tris(4-methoxyphenyl)benzene-1,4-diamine

용매

ethyl acetate

—

hexanes

반응 조건

후처리

1. 1
   기타6. Anhydrous toluene (30.0 mL) was degassed
2. 2
   기타by sparging with nitrogen for 10 minutes in a dry 200 mL schlenk flask
3. 3
   workup.STIRRINGto stir at 90° C.
4. 4
   여과Upon the disappearance of the starting materials the mixture was filtered through Celite
5. 5
   세척eluting with ethyl acetate
6. 6
   기타The product was purified by flash chromatography (silica gel, 5:1 hexanes:ethyl acetate)
7. 7
   기타The solvent was removed under reduced pressure
8. 8
   기타The residual solvent was removed in vacuo (9.06 g, 90.6%)

실험 절차

6. Anhydrous toluene (30.0 mL) was degassed by sparging with nitrogen for 10 minutes in a dry 200 mL schlenk flask. Tri(tert-butyl) phosphine (0.187 g; 0.924 mmol) and Pd2(dba)3 (0.283 g, 0.309 mmol) were added and the mixture was allowed to stir. After 10 minutes, 4-bromo-N,N-bis(4-methoxyphenyl)aniline (5.92 g; 15.4 mmol), 4-(3-(tert-butyldimethylsilyloxy)propoxy)-N-(4-methoxyphenyl)aniline (6.00 g; 15.4 mmol), and sodium tert-butoxide (2.08 g, 21.6 mmol) were added. The reaction was allowed to stir at 90° C. while being monitored by TLC (5:1 hexanes:ethyl acetate). Upon the disappearance of the starting materials the mixture was filtered through Celite eluting with ethyl acetate. The product was purified by flash chromatography (silica gel, 5:1 hexanes:ethyl acetate). The solvent was removed under reduced pressure. The residual solvent was removed in vacuo (9.06 g, 90.6%). 1H NMR (300 MHz, C3D6O) δ 6.98 (m, 8H), 6.86 (m, 8H), 6.82 (s, 4H), 4.06 (t, J=6.3 Hz, 2H), 3.83 (t, J=6.3 Hz, 2H), 3.76 (s, 9H), 1.95 (q, J=6.0 Hz, 2H), 0.890 (s, 9H), 0.058 (s, 6H). 13C {1H} NMR (300 MHz, C3D6O, δ): 156.40, 155.83, 143.65, 142.31, 126.24, 123.78, 116.04, 115.41, 65.28, 60.09, 55.63, 33.27, 26.23, −5.27. HRMS-EI (m/z): [M]+ calcd for C42H50N2O5Si, 690.35; found, 690.6). Anal. Calcd for C42H50N2O5Si: C, 73.01; H, 7.29; N, 4.05. Found: C, 73.25; H, 7.43; N, 4.01.

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