Hydrochloric Acid → Methyl 2-oxo-1-(propan-2-yl)cyclopentane-1-carboxylate

HRID 440573Notes

Reaction equation

HRID 440573 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])=[O:6].[CH:13](I)([CH3:15])[CH3:14].Cl>CN(C)C=O>[CH:13]([C:7]1([C:5]([O:4][CH3:3])=[O:6])[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 12586402Methyl 2-oxo-1-(propan-2-yl)cyclopentane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.7 g of sodium hydride (free of oil) was added to 80 ml of dimethylformamide. 25 g of 2-methoxycarbonylcylopentanone was slowly added dropwise while cooling with ice. The reaction mixture was allowed to come to room temperature, whereupon 45 g of isopropyl iodide was added, followed by stirring for a further 3.5 hours at 70°-80° C. The reaction mixture thus obtained was poured into 400 ml of 10% hydrochloric acid solution and extracted with 100 ml of ethyl acetate. The organic layer was washed with water, dried, and concentrated to obtain 25.5 g (yield, 78.7%) of the title compound.

Workup

  1. temperaturewhile cooling with ice
  2. additionwas added
  3. customThe reaction mixture thus obtained
  4. extractionextracted with 100 ml of ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customto obtain

Sources & evidence

ORD record
ord-90ed43350ad14b9496c8e09fe0dd327a
Source dataset
uspto-grants-1996_05
Patent number
US05519160

Reaction notes

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