Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate → 2-(2-oxocyclopentyl)acetic Acid

HRID 534269

Reaktionsgleichung

Reaktionsgleichung von HRID 534269
C([O:3][C:4](=[O:17])[CH2:5][C:6]1(C(OCC)=O)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])C>CC(O)=O.Cl>[O:11]=[C:7]1[CH2:8][CH2:9][CH2:10][CH:6]1[CH2:5][C:4]([OH:17])=[O:3]

Komponenten

4

Edukt 1

HCID 4418640Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate

Produkt 1

HCID 35699832-(2-oxocyclopentyl)acetic AcidAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

A solution of ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate (50.0 g, 206 mmol) in HOAc (500 mL) and 6 M HCl (250 mL) was heated at 100° C. for 6 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (500 mL) and H2O (200 mL). Aqueous layer was separated and extracted with EtOAc (2×250 mL). The combined organic layers were washed with H2O (300 mL), brine (300 mL), dried over Na2SO4, decanted and concentrated to yield the title compound as a white solid (22 g). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.72 (m, 1H), 1.75-1.90 (m, 1H), 2.03-2.10 (m, 1H), 2.20 (dd, J=10.9, 8.9 Hz, 1H), 2.30-2.40 (m, 2H), 2.40-2.50 (m, 2H), 2.80 (dd, J=15.7, 7.2 Hz, 1H), 11.5 (s, 1H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between EtOAc (500 mL) and H2O (200 mL)
  3. customAqueous layer was separated
  4. extractionextracted with EtOAc (2×250 mL)
  5. washThe combined organic layers were washed with H2O (300 mL), brine (300 mL)
  6. dry with materialdried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f2580b1065b54db4ac157f9301e3b30c
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853419B2

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