Potassium tert-butoxide → HCID 86704334, compound

HRID 516483Notes

Reaction equation

HRID 516483 reaction equation
C[C:2](C)([O-:4])C.[K+].[C:7]1([N:13]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[C:21]=3[C:29]3[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=3C=O)=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1COCC1>O1CCCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:37]1([N:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:14]2[CH:15]=[CH:16][C:17]([C:20]3[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[C:21]=3[C:29]3[CH:30]=[CH:33][C:34]([CH:2]=[O:4])=[CH:35][CH:36]=3)=[CH:18][CH:19]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86704335HCID 86704335, compound

Product 1

HCID 86704334HCID 86704334, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-(2-(4-(diphenylamino)phenyl)benzo[b]thiophen-3-yl)benzaldehyde (1.1 g, 0.0023 mol) was prepared in anhydrous tetrahydrofuran (75 mL). To a dry round bottom flask equipped with an addition funnel, methyltriphenylphosphonium bromide (1.22 g, 0.003 mol) was added. Tetrahydrofuran (75 mL) was added to this reaction flask and allowed to stir. Potassium tert-butoxide (0.40 g, 0.0035 mol) was then added. The solution of (2-(4-(diphenylamino)phenyl)benzo[b]thiophen-3-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 drop-wise. The reaction solution was allowed to stir for approximately 1 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. And the resulting solids were placed under vacuum. Crude mixture was purified by chromatography. Precipitation from a minimum amount of ethyl acetate into methanol yielded 1H NMR pure product. Product obtained: 0.7 g

Workup

  1. customTo a dry round bottom flask equipped with an addition funnel
  2. additionThis solution was then added to the reaction flask from the addition funnel drop-wise
  3. stirringto stir for approximately 1 hour
  4. filtrationthe reaction solution was filtered through a celite/silica gel (treated with triethylamine) plug
  5. customSolvent was removed by rotary evaporation
  6. customCrude mixture was purified by chromatography
  7. customPrecipitation from a minimum amount of ethyl acetate into methanol
  8. customyielded 1H NMR pure product
  9. customProduct obtained

Sources & evidence

ORD record
ord-3e75ec6709074f42a2d733a4562a6ff6
Source dataset
uspto-grants-2015_08
Patent number
US09112157B2

Reaction notes

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