Ammonium Hydroxide → HCID 19010302, compound

HRID 1741616Notes

Reaction equation

HRID 1741616 reaction equation
C(O[CH:4]=[C:5]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C[N:19](C)[C:20]([C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)=[CH2:21].[OH-].[NH4+]>C(O)C>[O:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[N:19]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:21]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 12532901HCID 12532901, compound

Product 1

HCID 19010302HCID 19010302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 147 g of diethyl ethoxymethyleneoxalacetate in 600 mL of absolute ethanol is stirred at 5° C. while a solution of 68.8 g of 1-dimethylamino-1-(2-furyl)ethylene in 400 mL of absolute ethanol is added dropwise over 1 hour. After stirring for an additional 2 hours, the reaction mixture is treated with 250 mL of concentrated aqueous ammonium hydroxide. The resulting mixture is stirred at ambient temperature overnight and then concentrated in vacuo. Chromatography of the residue on silica gel using chloroform as eluant affords the desired product.

Workup

  1. additionis added dropwise over 1 hour
  2. stirringThe resulting mixture is stirred at ambient temperature overnight
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15b10fe39abc4557b842471558b604f3
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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