Trimethylsilylacetylene → 4-(Trimethylsilylethynyl)benzaldehyde

HRID 128808

Reaction equation

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

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 707414-Bromobenzaldehyde

Product 1

HCID 27716434-(Trimethylsilylethynyl)benzaldehyde

Procedure

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%).

Sources & evidence

ORD record: ord-95221e74419c4ae68a3338a64b69b627
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05464865

Linked notes

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