Triethylamine → (4-Bromo-thiophen-2-ylethynyl)-trimethyl-silane

HRID 271729

反応式

HRID 271729 の反応式
C(N(CC)CC)C.Br[C:9]1[S:10][CH:11]=[C:12]([Br:14])[CH:13]=1.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16]>C1COCC1.[Cu]I>[Br:14][C:12]1[CH:13]=[C:9]([C:16]#[C:15][Si:17]([CH3:20])([CH3:19])[CH3:18])[S:10][CH:11]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2724560Thiophene, 2,4-dibromo-

生成物 1

HCID 67364285(4-Bromo-thiophen-2-ylethynyl)-trimethyl-silane

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Under an argon atmosphere 0.37 g (1.94 mmol) CuI, 2.24 g (1.94 mmol) tetrakis-triphenylphosphane-palladium and 16.2 mL triethylamine are added to a solution of 10.0 g (38.85 mmol) 2,4-dibromothiophene in 300 mL THF, the reaction mixture is cooled to −78° C. and then at this temperature a solution of 5.6 mL (38.85 mmol) ethynyl-trimethyl-silane in 250 mL THF is slowly added dropwise. After the addition has ended the mixture is allowed to heat up slowly to RT and stirred overnight. The mixture is evaporated down i.vac., the residue is combined with water, extracted exhaustively with DCM and the combined organic phases are dried over MgSO4. After the desiccant and solvent have been eliminated the residue is triturated with PE, filtered to remove insoluble ingredients and the solvent is evaporated down. The residue is purified by chromatography (silica gel, PE).

後処理

  1. additionAfter the addition
  2. temperatureto heat up slowly to RT
  3. customThe mixture is evaporated down i.vac
  4. extractionextracted exhaustively with DCM
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. customis triturated with PE
  7. filtrationfiltered
  8. customto remove insoluble ingredients
  9. customthe solvent is evaporated down
  10. customThe residue is purified by chromatography (silica gel, PE)

出典と根拠

ORDレコード
ord-c8b60b39523b4910834b0eeac7c0c3b7
出典データセット
uspto-grants-2008_11
特許番号
US07452911B2

関連ノート

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