Ethanol → Ethyl cyclopentanecarboxylate

HRID 2202677Notes

Reaction equation

HRID 2202677 reaction equation
[CH:1]1([C:6]([O-:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.OS(O)(=O)=O.C([O-])(O)=O.[Na+].[CH3:19][CH2:20]O>>[CH:1]1([C:6]([O:8][CH2:19][CH3:20])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Conditions

Temperature
80 °C

Procedure

To a solution of cyclopentanecarboxylate (1.14 g, 10 mmol) in EtOH (5 mL) was added H2SO4 (0.1 mL) at room temperature. The mixture was allowed to warm to 80° C. and stirred at the same temperature for 3.5 h. The reaction mixture was cooled down to room temperature and poured into saturated NaHCO3 aq. (40 mL). The mixture was stirred at room temperature for 30 min and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated under reduced pressure to provide compound A124-1 (1.01 g, 71%) as a pale yellow oil. The crude product was used for next step without purification.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customto provide compound A124-1 (1.01 g, 71%) as a pale yellow oil
  7. customThe crude product was used for next step without purification

Sources & evidence

ORD record
ord-4f0ec923f8b94dfa9c4b55d30a00c451
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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