Aluminum → HCID 86704337, compound

HRID 516484Notes

Reaction equation

HRID 516484 reaction equation
CC(C)([O-])C.[K+].[Al].[C:8]1([N:14]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]4[CH:37]=[CH:36][CH:35]=[CH:34][C:23]=4[S:24][C:25]=3[C:26]3[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1COCC1>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:38]1([N:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:16]=[CH:17][C:18]([C:21]3[C:22]4[CH:37]=[CH:36][CH:35]=[CH:34][C:23]=4[S:24][C:25]=3[C:26]3[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=3)=[CH:19][CH:20]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 3

HCID 5359268AluminumHCID 23665647Potassium tert-butoxideHCID 86704338HCID 86704338, compound

Product 1

HCID 86704337HCID 86704337, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(3-(4-(diphenylamino)phenyl)benzo[b]thiophen-2-yl)benzaldehyde (1.4 g, 0.0029 mol) was prepared in anhydrous THF (50 mL) in a clean, dry, and purged round bottom flask. To a dry round bottom flask equipped with an addition funnel methyltriphenylphosphonium bromide (1.82 g, 0.0051 mol) was added. Tetrahydrofuran (70 mL) was added to this reaction flask. Potassium tert-butoxide (0.59 g, 0.0052 mol) was then added to the reaction flask, and the flask was subsequently covered with aluminum foil. The solution of 4-(3-(4-(diphenylamino)phenyl)benzo[b]thiophen-2-yl)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. The reaction solution was allowed to stir for approximately 1 hour and completion was then confirmed via thin-layer chromatography. The reaction solution was filtered through a celite/silica gel (treated w/Et3N) plug. Solvent was removed by rotary evaporation. The resulting crude mixture was purified by chromatography on silica gel using ethyl acetate/hexane as an eluent. Precipitation from a minimum amount of ethyl acetate into methanol provided 1H NMR pure product. Product obtained: 1.06 g

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
  5. filtrationThe reaction solution was filtered through a celite/silica gel (treated w/Et3N) plug
  6. customSolvent was removed by rotary evaporation
  7. customThe resulting crude mixture was purified by chromatography on silica gel
  8. customPrecipitation from a minimum amount of ethyl acetate into methanol
  9. customprovided 1H NMR pure product
  10. customProduct obtained

Sources & evidence

ORD record
ord-174000a060894199a8d2a386cbbb708e
Source dataset
uspto-grants-2015_08
Patent number
US09112157B2

Reaction notes

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