Réaction #49845

Équation de réaction

6-benzyloxy

6-Benzyloxymethyl-2-methyl-5,6-dihydro-4H-pyran-4-one

→

title compound

Rendement 30.0%

5-Methyl-3-oxo-6,8-dioxabicyclo[3.2.1 ]octane

Rendement 30.0%

Solvants

EtOAc

Conditions de réaction

Traitement

1. 1
   FiltrationAfter completion, the reaction was filtered on a bed of celite
2. 2
   Autreevaporated to dryness
3. 3
   workup.ADDITIONcontaining 1 g of camphor sulphonic acid
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutrePurification by flash chromatography (30% Et2O/pentane)

Mode opératoire

A solution of 4.4 g of the 6-benzyloxy compound from Step 2 in EtOAc was hydrogenated with H2 and Pd/C (10%). After completion, the reaction was filtered on a bed of celite and then evaporated to dryness. The cru syrup was then taken up in CH2C2 containing 1 g of camphor sulphonic acid. The reaction was stirred at r.t. overnight, filtered and evaporated. Purification by flash chromatography (30% Et2O/pentane) gave 780 mg of the title compound (30%).

Source