Bromopinacolone → HCID 54360692, compound

HRID 1768596Notes

Reaction equation

HRID 1768596 reaction equation
[C:1]1([CH2:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].Br[CH2:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30]>CN(C)C=O>[CH3:30][C:29]([CH3:32])([CH3:31])[C:28](=[O:33])[CH2:27][C:12]([CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 21642BromopinacoloneHCID 9972002Diethyl (1-naphthyl)methylmalonateHCID 10942334Sodium Methoxide

Product 1

HCID 54360692HCID 54360692, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5.00 g (16.9 mmole) of diethyl (1-naphthylmethyl)malonate were dissolved in 50 ml of anhydrous dimethylformamide, and 1.00 g (18.5 mmole) of sodium methoxide was added to the solution, whilst ice-cooling, after which the mixture was stirred for 30 minutes. At the end of this time, a solution of 3.31 g (18.5 mmole) of 1-bromopinacolone (i.e. 1-bromo-3,3-dimethyl-2-butanone) dissolved in 10 ml of anhydrous dimethylformamide was added dropwise to the mixture, which was then stirred overnight at room temperature. The solvent was then removed by distillation under reduced pressure, and the resulting residue was mixed with a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 6: 1 by volume mixture of hexane and ethyl acetate), to afford 5.51 g (82%) of the title compound as a colorless oil.

Workup

  1. temperaturecooling
  2. additionwas added dropwise to the mixture, which
  3. stirringwas then stirred overnight at room temperature
  4. customThe solvent was then removed by distillation under reduced pressure
  5. additionthe resulting residue was mixed with a saturated aqueous solution of sodium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe residue was purified by column chromatography through silica gel (eluent
  10. additiona 6: 1 by volume mixture of hexane and ethyl acetate),

Sources & evidence

ORD record
ord-01780cc8cf414b278172da31c75452f7
Source dataset
uspto-grants-1995_01
Patent number
US05378690

Reaction notes

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