Réaction #2507818

Équation de réaction

caesium carbonate

o-phenylphenol

6-fluoro-7-iodo-3-propylchroman

diethyl malonate

→

Diethyl 2-(6-fluoro-3-propylchroman-7-yl)malonate

Solvants

ether

THF

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is heated
2. 2
   Températureunder reflux overnight
3. 3
   Lavageis washed with dil. hydrochloric acid
4. 4
   Séchagedried over sodium sulfate
5. 5
   AutreThe solvent is removed in vacuo
6. 6
   Autrethe crude product is purified by chromatography on silica gel with heptane/ethyl acetate (4:1)
7. 7
   AutreThe product fraction (Rf=0.55) is reacted without further purification

Mode opératoire

17.0 g (52.2 mmol) of anhydrous caesium carbonate, 700 mg (3.67 mmol) of copper(I) iodide and 700 mg (4.11 mmol) of o-phenylphenol are initially introduced under dry nitrogen, a solution of 11.4 g (33.5 mmol) of 6-fluoro-7-iodo-3-propylchroman and 16.0 g (100 mmol) of diethyl malonate in 150 ml of THF is added, and the mixture is heated under reflux overnight. MTB ether is subsequently added to the batch, which is washed with dil. hydrochloric acid and dried over sodium sulfate. The solvent is removed in vacuo, and the crude product is purified by chromatography on silica gel with heptane/ethyl acetate (4:1). The product fraction (Rf=0.55) is reacted without further purification.

Source