Diethyl Malonate → HCID 70094731, compound

HRID 2187391Notes

Reaction equation

HRID 2187391 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:15])[CH2:11][CH2:12][CH:13]=[CH2:14])=[CH:4][N:3]=1.[C:16]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].CC[O-].[Na+]>CCO>[CH2:21]([O:20][C:18](=[O:19])[CH:17]([C:16]([O:24][CH2:25][CH3:26])=[O:23])[CH:8]([C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[N:3][CH:4]=1)[CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH:13]=[CH2:14])[CH3:22]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 700932381-(2-Methyl-5-pyrimidinyl)-1,6-heptadien-3-one

Product 1

HCID 70094731HCID 70094731, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The enone 15-3 (5.73 g, 28.4 mmol) was dissolved in TBF (200 mL) and EtOH (80 mL) at room temperature. To this was added diethyl malonate (6.46 mL, 42.5 mmol) and NaOEt (1 mL, 2.8 mmol) and the mixture stirred for 1.5 hours. The solution was partitioned between saturated NaHCO3 solution and EtOAc, washed with water, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with EtOAc) to give the diester 15-4 as an oil.

Workup

  1. customat room temperature
  2. customThe solution was partitioned between saturated NaHCO3 solution and EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-0b6dc602add04620a709684dd22a9d42
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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