Réaction #2507819

Équation de réaction

diisobutylaluminium hydride

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

hydrochloric acid

→

2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe batch is subsequently added to ice-cold sat. ammonium chloride soln
2. 2
   Extractionextracted with MTB ether
3. 3
   Séchagephases are dried over sodium sulfate
4. 4
   Autreevaporated

Mode opératoire

8.7 g (21.1 mmol) of the diethyl 2-(6-fluoro-3-propylchroman-7-yl)malonate obtained under 1.2. are initially introduced in 60 ml of toluene, and 106 ml (106 mmol) of a 1 M solution of diisobutylaluminium hydride in toluene are added dropwise at 5° C. The batch is subsequently added to ice-cold sat. ammonium chloride soln., acidified using dil. hydrochloric acid and extracted with MTB ether. The combined org. phases are dried over sodium sulfate and evaporated. Chromatography of the crude product on silica gel with MTB ether/heptane (4:1) gives 2-(6-fluoro-3-propylchroman-7-yl)propane-1,3-diol as a colourless solid.

Source