Isopropyl iodide → 2-Furyl-2-isopropylmalonic acid diethyl ester

HRID 1655759Notes

Reaction equation

HRID 1655759 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:18])[CH:7]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH:19](I)([CH3:21])[CH3:20]>O1CCCC1>[CH2:11]([O:10][C:8](=[O:9])[C:7]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)([CH:19]([CH3:21])[CH3:20])[C:6]([O:5][CH2:3][CH3:4])=[O:18])[CH3:12]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 128365772-Furylmalonic acid diethyl ester

Product 1

HCID 536718092-Furyl-2-isopropylmalonic acid diethyl esterYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

24 g (1 mol) of sodium hydride were suspended in 100 ml of absolute tetrahydrofuran. A solution of 218.4 g (0.97 mol) of 2-furylmalonic acid diethyl ester in 200 ml of absolute tetrahydrofuran was added dropwise. The temperature rose to 30° (blue suspension). After stirring at 30° for 30 minutes, 340 g (200 ml; 2 mol) of isopropyl iodide were added dropwise within 30 minutes. The reaction mixture was heated to reflux overnight, thereafter evaporated under reduced pressure, and dissolved in ether. After evaporation of the solvent, the remaining oily residue was distilled in a high vacuum, to obtain 240.6 g (92.5%) of 2-furyl-2-isopropylmalonic acid diethyl ester (purity 93.6%) in the form of a yellowish oil, boiling point 85°-88°/13 Pa.

Workup

  1. customrose to 30°
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. customevaporated under reduced pressure
  5. dissolutiondissolved in ether
  6. customAfter evaporation of the solvent
  7. distillationthe remaining oily residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-49c3755beb6f47d68a7066e80904f0d5
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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