Reaction #2507819

Reaction equation

diisobutylaluminium hydride

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

hydrochloric acid

→

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

Solvents

toluene

toluene

Conditions

Workup

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

Procedure

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