Diethyl Malonate → HCID 54122132, compound

HRID 2292396Notes

Reaction equation

HRID 2292396 reaction equation
[O-][CH2:2][CH3:3].[Na+].[Na].[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[CH2:15]([O:14][C:6]([CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:19]([CH2:20][CH2:21][CH2:22][CH2:2][CH3:3])[CH3:18])=[O:13])[CH3:16]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 80571-BromopentaneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 54122132HCID 54122132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Alcoholic sodium ethoxide, prepared from sodium (7.8 g, 0.34 mol) in super-dry ethanol (200 cm3) was cooled to ca. 50° C. and diethyl malonate (55 g, 0.34 mol) added slowly with vigorous stirring. 1-Bromopentane (49.5 g, 0.33 mol) was added gradually and the mixture refluxed until neutral to moist litmus (ca. 2 h). The solvent was removed in vacuo and water (200 cm3) added. The aqueous layer was extracted with diethyl ether (2×100 cm3) and the combined ethereal layers were dried (Na2SO4). The solvent was removed in vacuo and the pure product isolated by distillation under reduced pressure.

Workup

  1. temperaturethe mixture refluxed until neutral to moist litmus (ca. 2 h)
  2. customThe solvent was removed in vacuo and water (200 cm3)
  3. additionadded
  4. extractionThe aqueous layer was extracted with diethyl ether (2×100 cm3)
  5. dry with materialthe combined ethereal layers were dried (Na2SO4)
  6. customThe solvent was removed in vacuo
  7. customthe pure product isolated by distillation under reduced pressure

Sources & evidence

ORD record
ord-38560d9ccb1c4fca9bb3a269702a9422
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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