Reaktion #61288

Reaktionsgleichung

5-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

triphenylphosphine

Carbon tetrabromide

→

desired product

Ausbeute 78.4%

6-(3-Bromomethyl-pent-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

Ausbeute 78.4%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe solution was stirred at room temperature
2. 2
   Filtrationthe reaction was filtered
3. 3
   Sonstigethe solvent was removed in vacuo
4. 4
   SonstigeThe crude material was purified by silica gel chromatography

Vorschrift

5-Ethyl-6-(3-hydroxymethyl-pent-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (35.4 mg, 0.090 mmol) was dissolved in DCM (3.0 mL). Polymer-bound triphenylphosphine (3 mmol/g, 90.7 mg) was added, and the mixture was mechanically stirred at room temperature. Carbon tetrabromide (90.2 mg, 0.272 mmol) was added and the solution was stirred at room temperature. After 2 hours, the reaction was filtered and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography to provide 32.0 mg (78%) of the desired product. The material was used in the next step without further characterization.

Quelle