反应 #635023

反应方程式

4-Bromomethylbenzophenone

4-bromomethyl benzophenone

2-(N-Ethylanilino)ethanol

NaH

→

desired product ( XIV )

收率 80.0%

4-([N-Ethyl-N-phenyl-2-aminoethyl]oxymethyl) benzophenone

收率 80.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 72 hours
3. 3
   其他Excess solvent was removed in vacuo
4. 4
   workup.ADDITIONthe residue diluted with DCM
5. 5
   洗涤washed with water and NaHCO3 solution (sat.)
6. 6
   干燥dried (MgSO4) and solvent
7. 7
   其他removed under vacuum
8. 8
   其他The resulting oil was purified by flash chromatography
9. 9
   洗涤eluting with petroleum (bp 40-60° C.)

实验过程

2-(N-Ethylanilino)ethanol (3.03 g, 18.4 mmol, 1.2 eq) in THF (20 cm3) was treated with NaH (60% dispersion in oil, 524 mg, 13.1 mmol, 1.4 eq) and stirred at 20° C. for 1 hour. 4-Bromomethylbenzophenone (IX) (4.21 g, 15.3 mmol) was then added and stirring continued for 72 hours. Excess solvent was removed in vacuo and the residue diluted with DCM, washed with water and NaHCO3 solution (sat.), dried (MgSO4) and solvent removed under vacuum. The resulting oil was purified by flash chromatography, eluting with petroleum (bp 40-60° C.):EtOAc (9:1), to give the desired product (XIV) as a yellow oil (4.36 g, 80%), Rf=0.54 (4:1, petrol:EtOAc) (Found: C, 78.34; H, 6.86; N, 5.29. C24H25NO2 requires C, 80.19; H, 7.01; N, 3.90%); υmax (film/cm−1 1658 (s), 1598 (s), 1506 (s); δH (200 MHz; CDCl3) 1.22 (3H, t, J7, CH3), 3.49 (2H, q, J7, CH2CH3), 3.58-3.79 (4 H, m, OCH2CH2N), 4.66 (2H, s, ArCH2O), 6.69-6.79 (3H, m, ArH o- and p- to NR2), 7.28 (2H, dd, J7, 7, ArH m- to NR2), 7.46-7.68 (5H, m, ArH), 7.80-7.88 (4H, m, ArH o- to C═O); δC (50.3 MHz; CDCl3) 12.2 (CH3), 45.5 (NCH2CH3), 50.1 (NCH2CH2O), 68.5 (NCH2CH2O), 72.2 (ArCH2O), 111.8 (ArCH o- to NR2), 115.8 (ArCH p- to NR2), 127.0, 128.3, 129.3, 130.0 and 130.3 (ArCH o- and m- to C═O and ArCH m- to NR2), 132.4 (ArCH p- to C═O), 136.8 and 137.7 (40 ArCC═O), 143.2 (40 ArCCH2O), 147.7 (40 ArCNR2), 196.4 (C═O); n/z (APCI+) 360 ([M+H]+, 30%); HRMS C24H26O2N requires 360.1963; found 360.1963.

来源