Potassium Carbonate → HCID 86679336, compound

HRID 1464909Notes

Reaction equation

HRID 1464909 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH3:16])=[O:14].Br[CH2:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21]>C1(C)C=CC=CC=1>[CH3:21][C:20]([CH3:23])([CH3:22])[CH2:19][CH2:18][C:9]1([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:11][CH2:12][C:8]1=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 1371371-Bromo-3,3-dimethylbutane

Product 1

HCID 86679336HCID 86679336, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

117.0 g (846.0 mmol) of potassium carbonate are added to a solution consisting of 40.0 g (281.7 mmol) of methyl 2-oxocyclopentanecarboxylate in 160 ml of dry toluene. 93 g (563.4 mmol) of 1-bromo-3,3-dimethylbutane are then added dropwise, and the mixture is stirred at reflux for 14 hours. After the reaction has ended the mixture is cooled to room temperature and filtered off through Celite. The product is concentrated under reduced pressure and purified by column chromatography (silica gel 100-200 mesh, mobile phase: ethyl acetate 5%/petroleum ether). This gives 48 g (75% of theory) of methyl 1-(3,3-dimethylbutyl)-2-oxocyclopentanecarboxylate.

Workup

  1. temperatureat reflux for 14 hours
  2. filtrationfiltered off through Celite
  3. concentrationThe product is concentrated under reduced pressure
  4. custompurified by column chromatography (silica gel 100-200 mesh, mobile phase: ethyl acetate 5%/petroleum ether)

Sources & evidence

ORD record
ord-c30326b423814bd19567897690ebbd83
Source dataset
uspto-grants-2015_04
Patent number
US08999956B2

Reaction notes

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