Water → Methyl 2-((trimethylsilyl)ethynyl)benzoate

HRID 1802816

反応式

HRID 1802816 の反応式
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13].C(N(CC)CC)C.O>O1CCCC1.[Cu]I>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69273Methyl 4-iodobenzoate

生成物 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoate収率 100.2%

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

実験手順

20.60 g (78.61 mmol) of 4-Iodobenzoic acid methyl ester and 9.26 g (94.33 mmol) of ethynyl trimethylsilane were dissolved in 200 ml of tetrahydrofuran, and thereto 23.86 g (235.83 mmol) of triethylamine, 1.65 g (2.36 mmol) of dichloro(bistriphenylphosphine)palladium(II) and 0.45 g (2.36 mmol) of copper(I) iodide were added. The mixture was stirred at room temperature for 8 hours. At the end of reaction, added water and extracted with ethylacetate. The extract was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and separated by column chromatography to obtain trimethylsilylethynylbenzoic acid methyl ester 18.30 g (Yield 100%).

後処理

  1. customAt the end of reaction
  2. extractionextracted with ethylacetate
  3. washThe extract was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customseparated by column chromatography

出典と根拠

ORDレコード
ord-a38fee4a0dc94c7694a1e30f0d4038ba
出典データセット
uspto-grants-2013_01
特許番号
US08349885B2

関連ノート

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