Water → HCID 24977027, compound

HRID 1660094Notes

Reaction equation

HRID 1660094 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH:4](Br)[C:5](Br)([CH3:7])[CH3:6].[CH3:11][O:12][C:13](=[O:17])[CH2:14][C:15]#[N:16].C[O-].[Na+].O>CO.CCOCC>[CH3:11][O:12][C:13]([C:14]1([C:15]#[N:16])[C:5]([CH3:7])([CH3:6])[CH:4]1[C:3]([O:2][CH3:1])=[O:10])=[O:17]

Participants

7

Reactant 4

HCID 962WaterHCID 7747Methyl cyanoacetateHCID 10942334Sodium MethoxideHCID 13023655Methyl 2,3-dibromo-3-methylbutanoate

Product 1

HCID 24977027HCID 24977027, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
64 °C

Procedure

27.2 g (0.1 mol) of α,β-dibromo-isovaleric acid methyl ester were added dropwise to a solution of 19.9 g (0.2 mol) of cyanoacetic acid methyl ester and 10.8 g (0.2 mol) of sodium methylate in 50 ml of methanol at 20° C. The mixture was then heated to 64° C. for 5 hours. The solvent was then stripped off in vacuo. 100 ml of water and 100 ml of ether were added to the residue. The ether phase was separated off, dried over sodium sulphate and evaporated. The residue was fractionated twice. 12 g (57% of theory) of 3,3-dimethyl-1-cyano-cyclopropane-1,2-dicarboxylic acid dimethyl ester were obtained in the form of a colorless oil of boiling point 152° C./10 mm Hg.

Workup

  1. customThe ether phase was separated off
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-a54e72ab1ad24824a2a2c5bc029936ba
Source dataset
uspto-grants-1981_12
Patent number
US04307033

Reaction notes

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