Methyl cyanoacetate → HCID 86758384, compound

HRID 2230920Notes

Reaction equation

HRID 2230920 reaction equation
[Na:1].[CH:2](OCC)=[O:3].[C:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])#[N:8]>CO>[Na:1].[CH3:13][O:12][C:10](=[O:11])[C:9](=[CH:2][OH:3])[C:7]#[N:8]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 8025Ethyl formateHCID 5360545Sodium

Product 1

HCID 86758384HCID 86758384, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium metal (11.8 g, 0.511 mol) was dissolved in 450 mL of methanol and to this warm solution was added a solution of ethyl formate (104 g, 1.41 mol) and methyl cyanoacetate (43.8 g, 0.440 mol) over two minutes. A small amount of precipitate formed during the addition. The reaction mixture was heated to reflux and maintained there for 1.5 hours. The thick white suspension was allowed to cool to 20° C.-25° C. and the precipitate was filtered, washed with diethylether, and dried in vacuo at 45° C. to give 40.4 g (61.6%) of the title compound which was of sufficient purity for use in Preparation 6.

Workup

  1. customA small amount of precipitate formed during the addition
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperaturemaintained there for 1.5 hours
  5. temperatureto cool to 20° C.-25° C.
  6. filtrationthe precipitate was filtered
  7. washwashed with diethylether
  8. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-fa8c9498ce0547b2b72188dd66fedf8c
Source dataset
uspto-grants-2002_07
Patent number
US06426417B1

Reaction notes

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