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

HRID 2369629
ノート
印刷プレビュー

反応式

HRID 2369629 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

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

生成物 1

HCID 671623681-(4-Pentylphenyl)ethynyl-3-triisopropylsiloxynaphthalene収率 33.1%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 3283Diethyl Ether溶媒
HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-26135af3f66d468e8ac5f8856bc1c2a3
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08703978B2

反応ノート

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