Diethyl Malonate → Diethyl isopentylmalonate

HRID 1386448Notes

Reaction equation

HRID 1386448 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].[O-]CC.[Na+:16].[CH2:17](Br)[CH2:18][CH:19]([CH3:21])[CH3:20]>C(O)C>[O-:5][CH2:4][CH3:3].[Na+:16].[CH2:17]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 78911-Bromo-3-methylbutaneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 2

HCID 79384Diethyl isopentylmalonateHCID 2723922Sodium ethoxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

Sodium ethoxide was prepared from sodium metal (9.1 g) and freshly distilled absolute ethanol (250 ml). Diethyl malonate (63.5 g) was added to sodium ethoxide in ethanol, and the mixture was stirred at 60-70° C. for 50 min. Isoamyl bromide (60 g) was added, and the reaction mixture was heated under reflux overnight. After the usual work-up, the resulting crude product was distilled under reduced pressure to give diethyl isoamylmalonate. Yield: 71.7 g (78%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. distillationAfter the usual work-up, the resulting crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-3e6e5354634a4e83a3f611a200e552a8
Source dataset
uspto-grants-2001_07
Patent number
US06265440B1

Reaction notes

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