Diethyl (ethoxymethylene)malonate → HCID 178469940, compound

HRID 2279619Notes

Reaction equation

HRID 2279619 reaction equation
C([O:3][CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](OCC)=O)C.[NH2:16][NH2:17].[OH-].[Na+]>CCO>[OH:3][C:4]1[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][NH:17][N:16]=1

Participants

5

Reactant 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 9321HydrazineHCID 14798Sodium Hydroxide

Product 1

HCID 178469940HCID 178469940, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diethyl (ethoxymethylene)malonate (20 g, 92.5 mmol) in 200 mL of EtOH is treated with hydrazine (2.9 mL, 92.5 mmol) by dropwise addition. After 10 min, 100 mL of 1 N NaOH is added (slightly exothermic), and the reaction mixture is stirred for a further 30 min. The EtOH is removed in vacuo, and the aqueous solution is diluted with a little more water and extracted with EtOAc. The aqueous phase is cooled to 0° C. and acidified to pH=5 with conc. HCl. The resulting precipitate is collected by vacuum filtration and dried in vacuo to give the title compound as an off-white solid.

Workup

  1. customThe EtOH is removed in vacuo
  2. additionthe aqueous solution is diluted with a little more water
  3. extractionextracted with EtOAc
  4. filtrationThe resulting precipitate is collected by vacuum filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-878cd577c6b8488382264c5b2c3d37fb
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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