Tetrahydrofuran → 3-(4-((4-(Bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propan-1-ol

HRID 2041849Notes

Reaction equation

HRID 2041849 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)[C:20]2[CH:25]=[CH:24][C:23]([N:26]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([N:26]([C:35]2[CH:36]=[CH:37][C:38]([O:41][CH3:42])=[CH:39][CH:40]=2)[C:23]2[CH:22]=[CH:21][C:20]([N:19]([C:43]3[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=3)[C:16]3[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67159432HCID 67159432, compound

Product 1

HCID 667303783-(4-((4-(Bis(4-methoxyphenyl)amino)phenyl)(4-methoxyphenyl)amino)phenoxy)propan-1-olYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry 250 mL round bottom flask under nitrogen was added N1-(4-(3-(tert-butyldimethylsilyloxy)propoxy)phenyl)-N1,N4,N4-tris(4-methoxyphenyl)benzene-1,4-diamine (9.06 g, 13.1 mmol), tetrahydrofuran (12.4 mL), and tetrabutylammonium fluoride (8.21 g, 31.4 mmol). The reaction was allowed to stir at room temperature while being monitored by thin layer chromatography. Upon disappearance of the starting material the reaction mixture was poured into a separatory funnel containing 150 mL of cold water. The product was extracted using 3×75 mL ether. The organic layers were combined and dried over MgSO4. The drying agent was removed by filtration and the solvent was removed under reduced pressure. The material was purified by flash chromatography (silica gel, 1:2 hexanes:ethyl acetate) and recrystallization (methanol) to yield a white solid (5.93 g, 78.6%). 1H NMR (400 MHz, C3D6O) δ 6.97 (m, 8H), 6.85 (m, 8H), 6.81 (s, 4H), 4.07 (t, J=J=6.3 Hz, 2H), 3.78 (s, 9H), 3.71 (q, J=5.7 Hz, 2H), 3.63 (t, J=5.2 Hz, 2H), 1.93 (q, J=6.3 Hz, 2H). 1H NMR (400 MHz, C3D6O with D2O) δ 6.95 (m, 8H), 6.84 (m, 8H), 6.79 (s, 4H), 4.03 (t, J=6.3 Hz, 2H), 3.74 (s, 9H), 3.68 (t, J=6.2 Hz, 2H), 1.92 (q, J=6.3 Hz, 2H). 13C{1H} NMR (400 MHz, C3D6O) δ 156.29, 155.77, 143.59, 143.53, 142.22, 142.13, 126.17, 123.68, 123.64, 115.98, 115.37, 65.74, 58.80, 55.62, 33.11. HRMS-EI (m/z): [M]+ calcd for C36H36N2O5, 576.26; found, 576.4). Anal. Calcd for C36H36N2O5: C, 74.98; H, 6.39; N, 4.86. Found: C, 74.80; H, 6.25; N, 4.82.

Workup

  1. additionUpon disappearance of the starting material the reaction mixture was poured into a separatory funnel
  2. extractionThe product was extracted
  3. dry with materialdried over MgSO4
  4. customThe drying agent was removed by filtration
  5. customthe solvent was removed under reduced pressure
  6. customThe material was purified by flash chromatography (silica gel, 1:2 hexanes:ethyl acetate) and recrystallization (methanol)

Sources & evidence

ORD record
ord-4e4cb95fdf5d4cd99bc1239a12bb158d
Source dataset
uspto-grants-2013_11
Patent number
US08586208B2

Reaction notes

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