Hydrochloric Acid → HCID 54396317, compound

HRID 1860530Notes

Reaction equation

HRID 1860530 reaction equation
COC(=O)CC[CH2:6][CH2:7][CH2:8][CH:9]=[C:10]1[CH2:14][CH2:13][CH2:12][C:11]1=[O:15].Cl.[C:18](=O)(O)[O-].[Na+].[C:23]([O:26][CH2:27]C)(=[O:25])[CH3:24]>CO>[CH3:27][O:26][C:23](=[O:25])[CH2:24][CH2:6][CH2:7][CH2:8][CH:9]([C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 57117051HCID 57117051, compound

Product 1

HCID 54396317HCID 54396317, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(2-oxo-cyclopentylidene)-heptanoic acid methyl ester obtained in Step B in methanol (1000 mL) was added concentrated hydrochloric acid (100 mL) and the reaction was heated at reflux for 20 h. The reaction mixture was cooled and was diluted with ethyl acetate. The organic solution was neutralized with aqueous sodium bicarbonate, dried (magnesium sulfate), filtered, and concentrated. Purification by distillation (145-155° C. at about 0.2 mmHg) provided 40 g of the title compound of Step C. 1H NMR (CDCl3, 250 MHz) d 7.28 (m, 1H), 3.65 (s, 3H), 2.54 (t, 2H), 2.38 (m, 2H), 2.28 (t, 2H), 2.14 (m, 2H), 1.61 (m, 2H), 1.45 (m, 2H), 1.31 (m, 4H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 20 h
  3. temperatureThe reaction mixture was cooled
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification
  8. distillationby distillation (145-155° C. at about 0.2 mmHg)

Sources & evidence

ORD record
ord-92fa9a5520464e2f8c638cb833a9abfc
Source dataset
uspto-grants-2003_03
Patent number
US06531485B2

Reaction notes

Loading…