Water → Methyl 4-cyano-3-oxobutanoate

HRID 1837321Notes

Reaction equation

HRID 1837321 reaction equation
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6](=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].O>CO.S(=O)(=O)(O)O>[C:1]([CH2:5][C:6](=[O:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 36240Methyl 4-chloroacetoacetate

Product 1

HCID 9964118Methyl 4-cyano-3-oxobutanoateYield 69.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

After 0.4 g of potassium cyanide was added at room temperature to a solution of 1 g of Methyl 4-chloro-3-oxobutanoate in 20 ml of methanol, the resulting mixture was warmed to 40° C. and maintained for further 8 hours. Thereafter, reaction solution was cooled and pH of the solution was adjusted to 3 by adding 10 ml of water and a few drops of concentrated sulfuric acid. After the mixture was extracted thrice with diethyl ether, total amount of which was 100 ml, the separated organic layers were combined and concentrated under reduced pressure to give 0.6 g of methyl 4-cyano-3-oxobutanoate (Purity: 71%).

Workup

  1. temperaturemaintained for further 8 hours
  2. customThereafter, reaction solution
  3. temperaturewas cooled
  4. extractionAfter the mixture was extracted thrice with diethyl ether, total amount of which
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bbd713c8be34d339bac4ee9bd7ed0f1
Source dataset
uspto-grants-2004_08
Patent number
US06781009B2

Reaction notes

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