Aluminum → HCID 86704339, compound

HRID 516485Notes

Reaction equation

HRID 516485 reaction equation
CC(C)([O-])C.[K+].[Al].[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:25]2[CH:37]=[CH:36][C:35]3[C:34]4[C:29](=[CH:30][C:31]([C:38]5[CH:43]=[CH:42][C:41]([C:44]6[CH:49]=[CH:48][C:47]([N:50]([C:57]7[C:66]8[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=8)[CH:60]=[CH:59][CH:58]=7)[C:51]7[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=7)=[CH:46][CH:45]=6)=[CH:40][CH:39]=5)=[CH:32][CH:33]=4)[C:28]([CH2:76][CH2:77][CH2:78][C:79]4[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=4)([CH2:67][CH2:68][CH2:69][C:70]4[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=4)[C:27]=3[CH:26]=2)[C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=[O:21])=[CH:12][CH:11]=1)=[O:9].C1COCC1>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]([C:25]2[CH:37]=[CH:36][C:35]3[C:34]4[C:29](=[CH:30][C:31]([C:38]5[CH:43]=[CH:42][C:41]([C:44]6[CH:49]=[CH:48][C:47]([N:50]([C:57]7[C:66]8[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=8)[CH:60]=[CH:59][CH:58]=7)[C:51]7[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=7)=[CH:46][CH:45]=6)=[CH:40][CH:39]=5)=[CH:32][CH:33]=4)[C:28]([CH2:67][CH2:68][CH2:69][C:70]4[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=4)([CH2:76][CH2:77][CH2:78][C:79]4[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=4)[C:27]=3[CH:26]=2)[C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[CH:20]=[O:21])=[CH:12][CH:11]=1)=[O:9]

Participants

6

Reactant 3

HCID 5359268AluminumHCID 23665647Potassium tert-butoxideHCID 86704340HCID 86704340, compound

Product 1

HCID 86704339HCID 86704339, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-((4-formylphenyl)(7-(4′-(naphthalen-1-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)-9,9-bis(3-phenylpropyl)-9H-fluoren-2-yl)amino)benzaldehyde (1.88 g, 0.0019 mol) was prepared in anhydrous THF (100 mL) in a clean, dry, and purged round bottom flask. To a dry round bottom flask equipped with an addition funnel methyltriphenylphosphonium bromide (2.02 g, 0.0057 mol) was added. Tetrahydrofuran (200 mL) was added to this reaction flask. Potassium tert-butoxide (0.66 g, 0.0059 mol) was then added to the reaction flask, and the flask was subsequently covered with aluminum foil. The solution of 3-((4-formylphenyl)(7-(4′-(naphthalen-1-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)-9,9-bis(3-phenylpropyl)-9H-fluoren-2-yl)amino)benzaldehyde/THF was then transferred to the addition funnel via cannula. This solution was then added to the reaction flask from the addition funnel dropwise over the course of twenty minutes. The reaction solution was allowed to stir for approximately one hour and completion was then monitored via thin-layer chromatography. Following confirmation of completion, the reaction solution was filtered through a celite/silica gel (treated with triethylamine) plug. Solvent was removed by rotary evaporation. The resulting solids were placed under vacuum. Crude mixture was purified by chromatography using ethyl acetate/hexanes as an eluent. Precipitation from a minimum amount of ethyl acetate into methanol yielded NMR pure product.

Workup

  1. customdry
  2. custompurged round bottom flask
  3. additionwas added
  4. additionThis solution was then added to the reaction flask from the addition funnel dropwise over the course of twenty minutes
  5. filtrationthe reaction solution was filtered through a celite/silica gel (treated with triethylamine) plug
  6. customSolvent was removed by rotary evaporation
  7. customCrude mixture was purified by chromatography
  8. customPrecipitation from a minimum amount of ethyl acetate into methanol yielded NMR pure product

Sources & evidence

ORD record
ord-da63d2b13b574daf8f4e8319e0d0fdd4
Source dataset
uspto-grants-2015_08
Patent number
US09112157B2

Reaction notes

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