Reaktion #2469

ord-5e5ea1bad7f34a958fa0ed6555062f7d

Reaktionsgleichung

CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O
ester
CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O
methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CC(=O)[O-].[Na+]
sodium acetate
→
CCCCC[C@@H]1C(=O)CC[C@@H]1CC(=O)OC
methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate
Ausbeute 94.9%

Edukte

CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O
ester
CCCCC[C@H]1[C@@H](CC(=O)OC)CC[C@H]1O
methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
PCC
CC(=O)[O-].[Na+]
sodium acetate

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigedescribed in Example 1 d

Vorschrift

This ester (2.85 g) was then oxidized by means of PCC, in the presence of sodium acetate, in a manner analogous to the method described in Example 1 d), to yield 2.68 g of the desired methyl (+)-(1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate (colorless oil; purity 98.5%; yield 92.7%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05728866uspto-grants-1998_03