Reaction #1519100

Reaction equation

THF

lithium aluminium hydride

THF

→

7-oxanorborn-2-en-5-ylmethanol

Conditions

Workup

1. 1
   Otherquenched
2. 2
   workup.ADDITIONby cautiously adding an ice-water mixture
3. 3
   OtherThe organic phase was removed
4. 4
   Extractionthe aqueous phase extracted with ethyl acetate (3×200 ml)
5. 5
   WashThe combined organic phases were washed with water (600 ml) and saturated sodium chloride solution (600 ml)
6. 6
   Dryingdried over sodium sulphate
7. 7
   Concentrationconcentrated under reduced pressure

Procedure

A solution of methyl 7-oxanorborn-2-en-5-ylcarbonate (16.163 g, 105 mmol, see Example 1) in THF (75 ml) was added dropwise with stirring and under nitrogen to a suspension of lithium aluminium hydride (4.376 g, 115 mmol) in anhydrous THF (100 ml), in such a way that the solution boiled gently. The reaction mixture was subsequently stirred at room temperature for another 12 h and then quenched by cautiously adding an ice-water mixture. The organic phase was removed and the aqueous phase extracted with ethyl acetate (3×200 ml). The combined organic phases were washed with water (600 ml) and saturated sodium chloride solution (600 ml), dried over sodium sulphate and concentrated under reduced pressure.

Source