Reaktion #6152

Reaktionsgleichung

hydrogen

methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoate

ozone

ethyl acetate

→

methyl 5-formyl-(R)-3[(tetrahydro-2H- pyran-2-yl)oxy]pentanecarboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigewas hydrogenated at room temperature
3. 3
   Filtrationwas filtered off
4. 4
   Waschenwashed with ethyl acetate
5. 5
   Sonstigethe filtrate and washings were evaporated in vacuo

Vorschrift

A solution of 2.56 g of methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoate in 40 ml of ethyl acetate was treated with ozone at -75° C. After completion of the reaction 0.1 g of Pd-on-carbon was added thereto and the mixture was hydrogenated at room temperature. After the hydrogen uptake was finished the catalyst was filtered off and washed with ethyl acetate and the filtrate and washings were evaporated in vacuo. There was obtained methyl 5-formyl-(R)-3[(tetrahydro-2H- pyran-2-yl)oxy]pentanecarboxylate.

Quelle