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Triphenylphosphine → 1-(4-Pentylphenyl)ethynyl-3-triisopropylsiloxynaphthalene

HRID 2369629
Notes
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Reaction equation

HRID 2369629 reaction equation
[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[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)([CH3:3])[CH3:2].[CH2:23]([C:28]1[CH:33]=[CH:32][C:31]([C:34]#[CH:35])=[CH:30][CH:29]=1)[CH2:24][CH2:25][CH2:26][CH3:27].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CCN(CC)CC.CCOCC.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>[CH2:23]([C:28]1[CH:29]=[CH:30][C:31]([C:34]#[C:35][C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:6]([O:5][Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:1]([CH3:3])[CH3:2])[CH:7]=2)=[CH:32][CH:33]=1)[CH2:24][CH2:25][CH2:26][CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 11776TriphenylphosphineHCID 27751311-Ethynyl-4-pentylbenzeneHCID 671624644-Bromo-2-triisopropylsiloxynaphthalene

Product 1

HCID 671623681-(4-Pentylphenyl)ethynyl-3-triisopropylsiloxynaphthaleneYield 33.1%

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 3283Diethyl EtherSolvent
HCID 8471TriethylamineSolvent

Procedure

A solution of 3-triisopropylsilyoxy-1-bromonaphthalene (2.32 g, 6.1 mmol), (4-pentylphenyl)acetylene (1.58 g, 9.2 mmol), Pd(PPh3)2Cl2 (129 mg, 3 mol %), PPh3 (240 mg, 15 mol %) and CuI (88 mg, 7.5 mol %) in Et3N (20 mL) under N2 was heated at reflux for 4 h. The resulting mixture was cooled, diluted with Et2O, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica using hexanes as eluent. The solvent was removed under reduced pressure to give the title compound (0.95 g, 33%) as a pale yellow oil.

Workup

  1. temperatureat reflux for 4 h
  2. temperatureThe resulting mixture was cooled
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-26135af3f66d468e8ac5f8856bc1c2a3
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