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

HRID 424795

反応式

HRID 424795 の反応式
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1I.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.[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:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 69132Benzoic acid, 2-iodo-, methyl ester

生成物 1

HCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoate収率 85.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.

後処理

  1. customThe reaction mixture is degassed for 20 minutes with a stream of nitrogen
  2. concentrationthe reaction is concentrated
  3. customthe residue is chromatographed
  4. washeluting with 0 to 5% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-b3cb5dace8cb4b3cb449666ab2002aaa
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

関連ノート

読み込み中…