Potassium Iodide → Diethyl [5-(acetyloxy)pentyl](methyl)propanedioate

HRID 372889Notes

Reaction equation

HRID 372889 reaction equation
[H-].[Na+].[CH3:3][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[I-].[K+].[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Cl)(=[O:19])[CH3:18]>CN(C=O)C>[C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:4]([CH3:3])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11857Diethyl methylmalonateHCID 24758Sodium hydride2×HCID 885211-Pentanol, 5-chloro-, 1-acetate

Product 1

HCID 54079282Diethyl [5-(acetyloxy)pentyl](methyl)propanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (4.8 g., 0.2 mole) as a 50% suspension in mineral oil is washed with petroleum ether under nitrogen to remove the mineral oil, suspended in dry benzene (150 ml.), and the suspension cooled in an ice bath . Diethyl methylmalonate (34.8 g., 0.2 mole) dissolved in sieve dried DMF (150 ml.) is added to the suspension of sodium hydride dropwise. The mixture is allowed to stand overnight at room temperature. Potassium iodide (0.4 g.) and 5-acetoxypentyl chloride (32.9 g., 0.2 mole) are then added, and the mixture is heated for 24 hours at 125° in an oil bath. The reaction mixture is concentrated in vacuo, diluted with ether (200 ml.), and filtered to remove sodium chloride. The filtrate is washed with brine, dried over anhydrous magnesium sulfate and concentrated to yield 39.6 g. (66%) of oily product.

Workup

  1. customto remove the mineral oil
  2. temperaturethe suspension cooled in an ice bath
  3. temperaturethe mixture is heated for 24 hours at 125° in an oil bath
  4. concentrationThe reaction mixture is concentrated in vacuo
  5. additiondiluted with ether (200 ml.)
  6. filtrationfiltered
  7. customto remove sodium chloride
  8. washThe filtrate is washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customto yield 39.6 g

Sources & evidence

ORD record
ord-cc1a6400f1a540a1aa2355e5c993f28e
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

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