Ethanol → Ethyl 4-(2-oxopyrrolidin-1-yl)cyclohexane-1-carboxylate

HRID 2116764Notes

Reaction equation

HRID 2116764 reaction equation
[N:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:26](O)[CH3:27]>>[N:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([C:13]([O:15][CH2:26][CH3:27])=[O:14])[CH2:11][CH2:12]2)[CH2:5][CH2:4][CH2:3][C:2]1=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 11572026Trans-4-(2-oxo-pyrrolidin-1-yl)cyclohexanecarboxylic acid

Product 1

HCID 23115699Ethyl 4-(2-oxopyrrolidin-1-yl)cyclohexane-1-carboxylateYield 102%

Conditions

Temperature
10 °C

Procedure

To 4-(2-pyrrolidon-1-yl)cyclohexylcarboxylic acid are added ethanol (30 mL, 10V/W) and conc. sulfuric acid (0.4 g, 0.2 W/W), and the mixture is heated to reflux for 3.5 hours. After cooling the reaction solution to 10° C., sodium bicarbonate (powder) is thereto added. After foaming is stopped, ethanol is evaporated under reduced pressure. The residue is extracted with ethyl acetate and saturated brine. The resultant solution is dried over magnesium sulfate and evaporated to remove the solvent under reduced pressure to give ethyl 4-(2-pyrrolidon-1-yl)cyclohexylcarboxylate (oil, 2.3 g, 102%).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 3.5 hours
  3. customethanol is evaporated under reduced pressure
  4. extractionThe residue is extracted with ethyl acetate and saturated brine
  5. dry with materialThe resultant solution is dried over magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-e09600a75ac148709deffda14bde2324
Source dataset
uspto-grants-2008_10
Patent number
US07439368B2

Reaction notes

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