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

HRID 2106840

Reaktionsgleichung

Reaktionsgleichung von HRID 2106840
[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

Edukt 4

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 86743990methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86743989methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate

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-d3091c05e60444aa91f42d9845a762a2
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931463

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