Hexane → (9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane

HRID 458493

反応式

HRID 458493 の反応式
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=2[CH:3]=1.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33].CCCCCC>CCN(CC)CC.[Cu]I.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:23]([C:5]1([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4]2[CH:3]=[C:2]([C:36]#[C:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

参加物

8

反応物 3

HCID 8058HexaneHCID 66111TrimethylsilylacetyleneHCID 129646932-Bromo-9,9-di-n-octylfluorene2 回

生成物 1

HCID 18442167(9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane収率 86%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 8471Triethylamine溶媒

実験手順

To an ice-cold mixture of 2-bromo-9,9-dioctylfluorene (11.47 g, 24.4 mmol) in 100 mL Et3N was added copper (I) iodide (31.0 mg, 0.163 mmol), palladium (II) acetate (29.7 mg, 0.132 mmol) and triphenylphosphine (90.8 mg, 0.346 mmol). Trimethylsilyl acetylene (3.0 g, 30.5 mmol) was then added and the mixture stirred for 30 minutes followed by a further 30 minutes while warming to room temperature. The reaction mixture was next refluxed for 20 hours and then allowed to cool to room temperature. Thin layer chromatography (hexane as the mobile phase) showed the reaction to be complete and the formation of a reaction product with Rf value less than that of 2-bromo-9,9-dioctylfluorene. Petroleum ether was added to the reaction mixture and the insolubles filtered off. The filtrate was evaporated to dryness and the residual oil taken up in petroleum ether and washed successively with HCl (10%), NaHCO3 solution and water. Drying over magnesium sulfate and evaporation gave oil characterized as (9,9-Dioctyl-9H-fluoren-2-ylethynyl)-trimethylsilane (10.2 g, 86% yield).

後処理

  1. waitfollowed by a further 30 minutes
  2. temperatureThe reaction mixture was next refluxed for 20 hours
  3. temperatureto cool to room temperature
  4. customthe reaction
  5. filtrationthe insolubles filtered off
  6. customThe filtrate was evaporated to dryness
  7. washwashed successively with HCl (10%), NaHCO3 solution and water
  8. dry with materialDrying over magnesium sulfate and evaporation
  9. customgave oil

出典と根拠

ORDレコード
ord-5e2562b52e66439cbd6ed123e8fb6c3c
出典データセット
uspto-grants-2007_03
特許番号
US07192657B2

関連ノート

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