Dichloromethane → 2,2-Dimethylmalonic acid monocyclohexyl ester

HRID 2089643

Reaction equation

HRID 2089643 reaction equation
[CH:1]1([O:7][C:8](=[O:19])[C:9]([CH3:18])([CH3:17])[C:10]([O:12]C(C)(C)C)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl.C(O)(C(F)(F)F)=O>C(OCC)(=O)C>[CH:1]1([O:7][C:8](=[O:19])[C:9]([CH3:17])([CH3:18])[C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 674699762,2-Dimethylmalonic acid t-butyl ester cyclohexyl ester

Product 1

HCID 674699622,2-Dimethylmalonic acid monocyclohexyl esterYield 88.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,2-dimethylmalonic acid t-butyl ester cyclohexyl ester (817 mg) and dichloromethane (7.5 mL), TFA (1.5 mL) was added, and the resulting mixture was stirred at room temperature for 2.5 hours. To the resulting mixture, ethyl acetate (100 mL) was added. The resulting mixture was sequentially washed with water (30 mL) and saturated aqueous sodium chloride solution (30 mL), and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and toluene (10 mL) was added to the filtrate obtained, after which the filtrate was concentrated under reduced pressure to obtain the captioned compound (571 mg).

Workup

  1. additionwas added
  2. washThe resulting mixture was sequentially washed with water (30 mL) and saturated aqueous sodium chloride solution (30 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe resulting mixture was filtered
  5. additiontoluene (10 mL) was added to the filtrate
  6. customobtained
  7. concentrationafter which the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b1616e8029f455ca1a69618d8b86e7f
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Linked notes

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