Reaction #2507818

Reaction equation

caesium carbonate

o-phenylphenol

6-fluoro-7-iodo-3-propylchroman

diethyl malonate

→

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

Solvents

ether

THF

Conditions

Workup

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

Procedure

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