Dimethyl malonate → HCID 15594961, compound

HRID 648616Notes

Reaction equation

HRID 648616 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-70fb35ab36a74682a45a476de32c39f1
Source dataset
uspto-grants-1988_04
Patent number
US04735962

Reaction notes

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