Dimethyl malonate → HCID 15594961, compound

HRID 1905667Notes

Reaction equation

HRID 1905667 reaction equation
[C:1]([O:8]C)(=O)[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH3:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15]>>[CH2:14]([NH:15][C:1](=[O:8])[CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:13][CH2:12][CH2:11][CH3:10]

Participants

3

Reactant 2

HCID 7943Dimethyl malonateHCID 8060Pentylamine

Product 1

HCID 15594961HCID 15594961, compoundYield 44%

Procedure

Dimethyl malonate (3.2 g, 24 mmol) and n-amylamine (2.1 g, 24 mmol) were mixed at room temperature. After stirring one hour solid began to precipitate. Diisopropyl ether (10 ml) was added and the mixture was left overnight at room temperature. The reaction mixture was concentrated in vacuo. The residue was chromatographed on silica gel (100 g, Baker for flash chromatography), eluting with CH2Cl2 and 2% MeOH in CH2Cl2 to give the title compound as an oil (1.97 g, 44%).

Workup

  1. customto precipitate
  2. additionDiisopropyl ether (10 ml) was added
  3. waitthe mixture was left overnight at room temperature
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g, Baker for flash chromatography)
  6. washeluting with CH2Cl2 and 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-d3bbc92239f7491481f87c1638b03a5a
Source dataset
uspto-grants-1987_03
Patent number
US04647573

Reaction notes

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