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

HRID 62799

Reaction equation

HRID 62799 reaction equation
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]

Participants

4

Reactant 1

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

Product 1

HCID 35699832-(2-oxocyclopentyl)acetic AcidYield 75.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4505539facc24cffac6611ec5bf7f76f
Source dataset
uspto-grants-2016_09
Patent number
US09447041B2

Linked notes

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