Diethyl Malonate → diethyl 2-cyclohexylmethylmalonate

HRID 1060731Notes

Reaction equation

HRID 1060731 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:13]1([CH2:19]Br)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)C>[CH:13]1([CH2:19][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 137636Cyclohexane, (bromomethyl)-HCID 5360545Sodium

Product 1

HCID 599487diethyl 2-cyclohexylmethylmalonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution comprised of sodium (6.9 g, 0.3 mmol) in ethanol (250 mL) was treated sequentially with diethyl malonate (53.127 g, 0.3 mol) and then cyclohexylmethyl bromide (46 mL, 0.33 mol) at ambient temperature. The mixture was heated to 70° C. and stirred for approximately 12 hours. The mixture was cooled and solvent was removed by evaporation. The residue was diluted with ice water and the dilution was extracted with ethyl acetate (4×). The combined extracts were washed with water (4×) and brine, dried (MgSO4) and concentrated to provide diethyl 2-cyclohexylmethylmalonate.

Workup

  1. customat ambient temperature
  2. temperatureThe mixture was cooled
  3. customsolvent was removed by evaporation
  4. additionThe residue was diluted with ice water
  5. extractionthe dilution was extracted with ethyl acetate (4×)
  6. washThe combined extracts were washed with water (4×) and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f9599f35ecd5494fa60a52163df24231
Source dataset
uspto-grants-2003_02
Patent number
US06525036B2

Reaction notes

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