Dimethyl malonate → Dimethyl cyclopentane-1,1-dicarboxylate

HRID 409488

Reaction equation

HRID 409488 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+].F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:4]1([C:5]([O:7][CH3:8])=[O:6])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

7

Reactant 4

HCID 7943Dimethyl malonateHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27341781-Butyl-3-methylimidazolium tetrafluoroborate

Product 1

HCID 12609605Dimethyl cyclopentane-1,1-dicarboxylateYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of malonic acid dimethyl ester (5.28 g, 40 mmol) in DMF (100 mL), 1,4-dibromo-butane (5.26 mL, 44 mmol), K2CO3 (13.8 g, 100 mmol), 1-butyl-3-methylimidazolium tetrafluoroborate (0.904 g, 4.0 mmol) are added at room temperature. The mixture is stirred at room temperature for 15 hours. To the mixture, water is added and the solution is extracted with EtOAc. The organic layer is washed with H2O and brine, dried over MgSO4, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give cyclopentane-1,1-dicarboxylic acid dimethyl ester (6.13 g, 82%); TLC (hexane/AcOEt, 5:1) Rf 0.48.

Workup

  1. extractionthe solution is extracted with EtOAc
  2. washThe organic layer is washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ea1440a2f7a6420b874ee09574847f47
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Linked notes

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