Dimethyl malonate → HCID 18408270, compound

HRID 992839Notes

Reaction equation

HRID 992839 reaction equation
[Na].[C:2]([O:9][CH3:10])(=[O:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH3:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH:14](Br)[CH2:13]1>CO>[CH3:7][O:6][C:4](=[O:5])[CH:3]([CH:14]1[CH2:15][CH2:16][CH2:17][CH:12]([CH3:11])[CH2:13]1)[C:2]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 95431Cyclohexane, 1-bromo-3-methyl-HCID 5360545Sodium

Product 1

HCID 18408270HCID 18408270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium metal (7.02 g, 0.30 g atm) was reacted with anhydrous methanol (250 mL). To this was then added dimethyl malonate (70 mL) dropwise while the temperature of the reaction was maintained at 50° C. To this solution was then added dropwise 3-methylcyclohexylbromide (54.0 g, 0.30 mol) and the reaction refluxed overnight. The methanol was removed on a rotovap and the remaining material partitioned between ether and water. The ether layer was separated, dried with MgSO4 and evaporated to give a yellow oil. Distillation of the material at 95-106° C. and 1.2 mm pressure gave a clear oil.

Workup

  1. temperaturethe reaction refluxed overnight
  2. customThe methanol was removed on a rotovap
  3. customthe remaining material partitioned between ether and water
  4. customThe ether layer was separated
  5. dry with materialdried with MgSO4
  6. customevaporated
  7. customto give a yellow oil
  8. distillationDistillation of the material at 95-106° C.
  9. custom1.2 mm pressure gave a clear oil

Sources & evidence

ORD record
ord-419d5517aad6476488369dd13856f816
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

Loading…