Trimethylsilylacetylene → 1-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

HRID 1916521ノート

反応式

HRID 1916521 の反応式
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].I[C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1>N1CCCCC1.[Cu]I>[CH3:4][Si:3]([C:1]#[C:2][C:8]1[CH:21]=[CH:20][C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:9]=1)([CH3:6])[CH3:5]

参加物

5

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 219591661-(2-(4-Iodophenoxy)ethyl)pyrrolidine

生成物 1

HCID 673634551-[2-(4-Trimethylsilanylethynyl-phenoxy)-ethyl]-pyrrolidine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8082Piperidine溶媒

実験手順

Under a nitrogen atmosphere 7.0 mL (49.5 mmol) ethynyl-trimethyl-silane is slowly added to a mixture of 14.3 g (45 mmol) 1-[2-(4-iodo-phenoxy)-ethyl]-pyrrolidine, 1.04 g (0.9 mmol) tetrakis-triphenylphosphane-palladium and 171 mg (0.4 mmol) CuI in 140 mL piperidine (exothermic reaction) and stirred for 30 minutes. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

後処理

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

出典と根拠

ORDレコード
ord-f8d4ea79d767455ca8110c0dc05435f5
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

反応ノート

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