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

HRID 707769

Reaktionsgleichung

Reaktionsgleichung von HRID 707769
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-8b2288420534465cb7a76b895d39eb9e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175320B2

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