Trimethylsilylacetylene → 4-(Trimethylsilylethynyl)benzaldehyde

HRID 128808

반응식

HRID 128808 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>>[CH3:10][Si:11]([CH3:13])([CH3:12])[C:14]#[C:15][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

참가 물질

3

실험 절차

By the method of example 53(A), 4-bromobenzaldehyde is coupled with (trimethylsilyl)acetylene to provide 4-(2-(trimethylsilyl)ethynyl)benzaldehyde as a pale yellow solid after sublimation in vacuo. This material (5.8 g) is desilylated by stirring with potassium carbonate (0.4 g) in methanol (20 ml) for two hours. The solution is evaporated, and the product dissolved in methylene chloride, washed with water, dried, and concentrated to provide 4-ethynylbenzaldehyde as a yellow solid (3.45 g, 90%). By the Wittig reaction of example 1(A), this is chain-extended to provide 1-ethynyl-4-(2-methoxyethenyl)benzene, obtained as a colorless oil after distillation in vacuo (3.10 g, 77%).

출처 및 근거

ORD 기록
ord-95221e74419c4ae68a3338a64b69b627
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

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