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Triphenylphosphine → 3-[(4-Dibutylaminophenyl)ethynyl]-2-naphthol

HRID 2369633
Notes
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Reaction equation

HRID 2369633 reaction equation
C([Si](C(C)C)(C(C)C)[O:5][C:6]1[CH:7]=[C:8](Br)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(C)C.[C:23]([C:25]1[CH:39]=[CH:38][C:28]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)#[CH:24].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.O>[CH2:30]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[C:28]1[CH:27]=[CH:26][C:25]([C:23]#[C:24][C:7]2[C:6]([OH:5])=[CH:15][C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:39][CH:38]=1)[CH2:31][CH2:32][CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 11776TriphenylphosphineHCID 2724141Tetrabutylammonium FluorideHCID 12249159N,N-dibutyl-4-ethynylanilineHCID 671624644-Bromo-2-triisopropylsiloxynaphthalene

Product 1

HCID 671627463-[(4-Dibutylaminophenyl)ethynyl]-2-naphtholYield 44.9%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 962WaterSolvent2×
HCID 8471TriethylamineSolvent

Procedure

A solution of 3-triisopropylsilyoxy-1-bromonaphthalene (3.17 g, 8.4 mmol), 4-ethynyl-N,N-dibutylaniline (2.87 g, 12.5 mmol), Pd(PPh3)2Cl2 (176 mg, 3 mol %), PPh3 (329 mg, 15 mol %) and CuI (120 mg, 7.5 mol %) in Et3N (20 mL) under N2 was heated at reflux for 3 h. The resulting mixture was cooled, poured into water (200 mL), extracted with DCM (3×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using DCM (20% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue dissolved in Et2O (30 mL). Tetrabutylammonium fluoride (3.8 mL, 1 M, 3.8 mmol) was added and stirring continued for 10 min. The solution was poured into water (100 mL), extracted with Et2O (3×40 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (15% in hexanes to 0% in EtOAc gradient) as eluent. The solvent was removed under reduced pressure to give the title compound (1.40 g, 21%) as a brown oil.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureThe resulting mixture was cooled
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on silica
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe residue dissolved in Et2O (30 mL)
  9. extractionextracted with Et2O (3×40 mL)
  10. dry with materialdried (MgSO4)
  11. customthe solvent removed under reduced pressure
  12. filtrationThe residue was filtered through a short plug of silica
  13. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b5eb59f967454a239a0a5c7bf1eb10e6
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08703978B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes