Reaktion #216878

ord-c6d30e4bb6f0457993ca5a2a4f7ea51f

Reaktionsgleichung

COC(=O)c1cc(C(C)O)c2ccc(OCc3ccccc3)cc2c1
1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
COC(=O)c1cc(CC(=O)O)c2ccc(OCc3ccccc3)cc2c1
3-carbomethoxy-6-benzyloxy-1-naphthyl acetic acid

Edukte

COC(=O)c1cc(C(C)O)c2ccc(OCc3ccccc3)cc2c1
1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe mixture is partitioned between ethyl acetate and H2O
  2. 2
    TrocknenThe organics are dried (MgSO4)
  3. 3
    Einengenconcentrated in vacuo

Vorschrift

To a solution of 0.08 g (0.24 mmol) of 1-hydroxyethyl-3-carbomethoxy-6-benzyloxynaphthalene in 10 ml of acetone at 0° C. is added Jones reagent until a green precipitate forms. After stirring at 0° C. for 10 minutes, the mixture is partitioned between ethyl acetate and H2O. The organics are dried (MgSO4) and concentrated in vacuo to afford 0.081 g of 3-carbomethoxy-6-benzyloxy-1-naphthyl acetic acid in the form of a light tan solid which is used directly in the next step.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05468898uspto-grants-1995_11