Methanol → Diethyl 2-acetamido-2-(2-pentadecynyl)malonate

HRID 1451592Notes

Reaction equation

HRID 1451592 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[CH3:16][CH2:17][O-].[Na+].[CH2:20]([C:28]1[CH:33]=[CH:32][C:31](CCO)=[CH:30][CH:29]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]C.CO>C(O)C>[C:1]([NH:4][C:5]([CH2:26][C:25]#[C:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:17][CH3:16])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 113108762-(4-Octylphenyl)ethanol

Product 1

HCID 21849278Diethyl 2-acetamido-2-(2-pentadecynyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl acetamidomalonate (3.327 g) and 1.137 g of sodium ethylate were dissolved in 50 ml of dry ethanol and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. A solution of 4.000 g of the compound of (3) above in 30 ml of dry ethanol was added thereto and the mixture was refluxed for 15 hours. Methanol (50 ml) was added to the reaction mixture and the insoluble matters were removed. The solvent was distilled away under reduced pressure and the residue was purified by silica gel column chromatography to give 3.236 g of diethyl 2-acetamido-2-(2-pentadecynyl)malonate.

Workup

  1. temperaturethe mixture was refluxed for 15 hours
  2. customthe insoluble matters were removed
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ad12dc0fb1524e188118e1a7bc5d647c
Source dataset
uspto-grants-1997_02
Patent number
US05604229

Reaction notes

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