1,2-Dimethoxyethane → Vinyltriphenylamine

HRID 357467

Reaction equation

HRID 357467 reaction equation
[H-].[Na+].[C:3]1([N:9]([C:16]2[CH:23]=[CH:22][C:19](C=O)=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO[CH2:26][CH2:27]OC>[Br-].C[P+](C)(C)C.C(O)C>[CH:26]([C:17]1[CH:18]=[CH:19][CH:22]=[CH:23][C:16]=1[N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH2:27]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 77846Benzaldehyde, 4-(diphenylamino)-

Product 1

HCID 22283755Vinyltriphenylamine

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 357594Tetramethylphosphonium bromideCatalyst

Procedure

4.6 g of sodium hydride and 700 mL of 1, 2-dimethoxyethane were placed in a three-neck flask, and while stirring at room temperature, 130.8 g of tetramethylphosphonium bromide was added. After adding one drop of anhydrous ethanol, the mixture was stirred for 4 hours at 70° C. Then 100 g of 4-(N, N-diphenylamino) benzaldehyde was added; the mixture was hold at 70° C. for 5 hours. The solution was filtered, and an ether extract of the precipitate and the filtrate were washed with water. Next, the ether solution was dried over calcium chloride, the ether was removed, and the crude product was obtained. This was recrystallized from ethanol, and a needle-form, lemon- yellow vinyltriphenylamine was obtained. The yield was 83.4 g (84.0%). Synthesis of 4-[2 (triethoxysilyl) ethyl] triphenylamine 15 40 mL of toluene, 9.9 g (60 mmol) of triethoxysilane, and 0.018 mmol of a tris (tetramethyldivinyldisiloxane) platinum (0) complex in a toluene solution were placed in a three-neck flask, and while stirring under room temperature, 20 mL of a toluene solution of 8.2 g of 4-vinyltriphenylamine was added. Upon completion of the addition, the mixture was stirred for 3 hours at 70° C., then the. solvent was removed under reduced pressure. As a result, a lemon-yellow oily substance of 4-[2-(triethoxysilyl) ethyl] triphenylamine was obtained. The amount obtained was 12.1 g (91.7%).

Workup

  1. stirringthe mixture was stirred for 4 hours at 70° C
  2. customat 70° C.
  3. customfor 5 hours
  4. filtrationThe solution was filtered
  5. extractionan ether extract of the precipitate
  6. washthe filtrate were washed with water
  7. dry with materialNext, the ether solution was dried over calcium chloride
  8. customthe ether was removed
  9. customthe crude product was obtained
  10. customThis was recrystallized from ethanol

Sources & evidence

ORD record
ord-f33462516e98432db9f2e07a97c7c52e
Source dataset
uspto-grants-1998_11
Patent number
US05840816

Linked notes

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