Trimethylsilylacetylene → ((4-(tert-Butyl)phenyl)ethynyl)trimethylsilane

HRID 257986

반응식

HRID 257986 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>[Pd](Cl)Cl.C(N(CC)CC)C>[CH3:12][Si:13]([C:16]#[C:17][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1)([CH3:15])[CH3:14]

참가 물질

5

반응물 2

HCID 66111Trimethylsilylacetylene2회HCID 775951-Bromo-4-tert-butylbenzene2회

생성물 1

HCID 14989664((4-(tert-Butyl)phenyl)ethynyl)trimethylsilane

시약·촉매·용매 2

HCID 24290Palladium Chloride촉매HCID 8471Triethylamine용매

반응 조건

온도
67.5 °C

실험 절차

A stirred mixture of 3.05 g (14. 31 mmol) of 4-tert-butyl-bromobenzene (Compound 20), 1.41 g (14.39 mmol) of trimethylsilylacetylene (Compound 16), 139 mg (0.13 mmol) of cuprous iodide, 293 mg (0.42 mmol) of bis(triphenyophosphine) palladium (II) chloride and 3 ml of triethylamine was flushed with nitrogen and then heated under nitrogen at 65-70 degrees C. for 20 hours. The reaction mixture was stirred at room temperature for a further 4 hours and the triethylamine then removed under vacuum. The residue was purified by flash chromatography (silica; hexanes) to give the title compound as a colorless oil. PMR (CDCl3): & 0.26 (9H, s), 1.31 (9H, s), 7.32 (2H, d, J~8.2 Hz), 7.42 (2H, d, J~8.2 HZ).

후처리

  1. customwas flushed with nitrogen
  2. customthe triethylamine then removed under vacuum
  3. customThe residue was purified by flash chromatography (silica; hexanes)

출처 및 근거

ORD 기록
ord-27c26387f1a14287aff289b9d3224ee1
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264456

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