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

HRID 436246

Reaction equation

[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]

Participants

Reactant 3

HCID 24425Chromic Acid

HCID 3431174-Oxocyclopent-2-en-1-yl acetate

HCID 12773776(1S,4S)-4-hydroxycyclopent-2-en-1-yl acetate

Product 1

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

Procedure

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°.

Workup

customto be +74°

Sources & evidence

ORD record: ord-616c92a305f34e4c8fe816b4522a6aaf
Source dataset: uspto-grants-1977_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04008125

Linked notes

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