Chloride → HCID 54516793、化合物

HRID 55296ノート

反応式

HRID 55296 の反応式
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[Cl-]>C(N(CC)CC)C.[Cu]I>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])=[CH:7][CH:6]=1

参加物

6

反応物 3

HCID 312ChlorideHCID 66111TrimethylsilylacetyleneHCID 316783Methyl 2-(4-bromophenyl)acetate

生成物 1

HCID 54516793HCID 54516793、化合物収率 79.5%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8471Triethylamine溶媒

実験手順

A solution of 20 g of 4-bromophenylacetic acid methyl ester and 10.3 g of trimethylsilylacetylene in 650 ml of triethylamine is refluxed in the presence of 1.46 g of bis-triphenylphosphinepalladium(II) chloride and 227 mg of copper(I) iodide for 5 hours. The reaction mixture is concentrated by evaporation, the residue is spread between water and ethyl acetate, the organic phase is washed with saturated common salt solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/0-5% ethyl acetate. 17.1 g of 4-(2-trimethylsilylethinyl)-phenylacetic acid methyl ester is obtained as oily crude product.

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. washthe organic phase is washed with saturated common salt solution
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with hexane/0-5% ethyl acetate

出典と根拠

ORDレコード
ord-1dfc0b0dda894b629602d5f73bc01a98
出典データセット
uspto-grants-1997_04
特許番号
US05624943

反応ノート

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