Reaction #2507829

Reaction equation

6-fluoro-3-pentylchroman-7-carbaldehyde

sodium borohydride

→

(6-fluoro-3-pentylchroman-7-yl)methanol

Solvents

water

ethanol

Conditions

Workup

1. 1
   Extractionextracted three times with MTB ether
2. 2
   Washphases are washed with sat. sodium chloride soln
3. 3
   Dryingand dried over sodium sulfate
4. 4
   Otherthe solvent is removed in vacuo
5. 5
   Filtrationthe residue is filtered through silica gel with dichloromethane (Rf=0.3)

Procedure

11.1 g (44.3 mmol) of 6-fluoro-3-pentylchroman-7-carbaldehyde are dissolved in 100 ml of ethanol, and 2.0 g (52.8 mmol) of sodium borohydride are added in portions. After 3 h, the batch is diluted with water and extracted three times with MTB ether. The combined org. phases are washed with sat. sodium chloride soln. and dried over sodium sulfate, the solvent is removed in vacuo, and the residue is filtered through silica gel with dichloromethane (Rf=0.3), giving (6-fluoro-3-pentylchroman-7-yl)methanol as a colourless solid.

Source