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

HRID 1916521노트

반응식

HRID 1916521 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8082Piperidine용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f8d4ea79d767455ca8110c0dc05435f5
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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