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

HRID 6056

Reaktionsgleichung

Reaktionsgleichung von HRID 6056
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:14][CH2:15][CH:16]=C)[CH2:9][C:10](OC)=O.[O:18]=[O+][O-].[H][H].[C:23]([O:26][CH2:27]C)(=[O:25])C>>[CH:16]([CH2:15][CH2:14][C@@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:9][CH2:10][C:23]([O:26][CH3:27])=[O:25])=[O:18]

Komponenten

5

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added
  2. customwas hydrogenated at room temperature
  3. filtrationwas filtered off
  4. washwashed with ethyl acetate
  5. customthe filtrate and washings were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1961c38b3bfe41e9850737dd3646a122
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246960

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