Diisopropylamine → (Furan-2-ylethynyl)trimethylsilane

HRID 705002

反応式

HRID 705002 の反応式
Br[C:2]1[O:3][CH:4]=[CH:5][CH:6]=1.C(NC(C)C)(C)C.C1COCC1.[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>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>[O:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19]

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 8028TetrahydrofuranHCID 66111TrimethylsilylacetyleneHCID 2776190Furan, 2-bromo-

生成物 1

HCID 11217431(Furan-2-ylethynyl)trimethylsilane収率 35.84%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

実験手順

A mixture of 2-bromofuran (500 mg, 3.402 mmol), Pd(PPh3)2Cl2 (75.69 mg, 0.10784 mmol), CuI (40.17 mg, 0.2109 mmol) and diisopropylamine (0.89 ml, 6.395 mmol) in tetrahydrofuaran (THF) (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.648 ml, 4.694 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield the desired (furan-2-ylethynyl)trimethylsilane (200 mg, 1.21 mmol, yield 35.84%).

後処理

  1. additionwas added at room temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe crude material was purified by column chromatography (100-200 mesh silica gel)

出典と根拠

ORDレコード
ord-8c0ad605730944dabba5b4e065da2eb3
出典データセット
uspto-grants-2015_11
特許番号
US09173401B2

関連ノート

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