Chromic Acid → 4-Cyclopentene-1,3-diol, 1-acetate, (1R,3S)-rel-

HRID 436246

Reaktionsgleichung

Reaktionsgleichung von HRID 436246
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([OH:10])[CH:7]=[CH:6]1)(=[O:3])[CH3:2].C(OC1CC(=O)C=C1)(=O)C.[Cr](O)(O)(=O)=O>>[C:1]([O:4][C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH:7]=[CH:6]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 24425Chromic AcidHCID 3431174-Oxocyclopent-2-en-1-yl acetateHCID 12773776(1S,4S)-4-hydroxycyclopent-2-en-1-yl acetate

Produkt 1

HCID 98554984-Cyclopentene-1,3-diol, 1-acetate, (1R,3S)-rel-

Versuchsvorschrift

The trans-3-acetoxy-5-hydroxycyclopent-1-ene obtained by using baker's yeast and whose absolute configuration was determined to be of R-configuration was converted to 4-acetoxycyclopent-2-en-1-one by oxidation with chromic acid. When the specific rotation of this compound was found to be +74°.

Aufarbeitung

  1. customto be +74°

Quellen und Nachweise

ORD-Eintrag
ord-616c92a305f34e4c8fe816b4522a6aaf
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008125

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