Cyanoacetic acid → (Trimethylsilyl)methyl cyanoacetate

HRID 1765915Notes

Reaction equation

HRID 1765915 reaction equation
[OH:1][CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[C:7]([CH2:9][C:10](O)=[O:11])#[N:8]>C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[C:7]([CH2:9][C:10]([O:1][CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])=[O:11])#[N:8]

Participants

5

Reactant 2

HCID 9740Cyanoacetic acidHCID 766921-(Trimethylsilyl)methanol

Product 1

HCID 14953601(Trimethylsilyl)methyl cyanoacetateYield 69.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 1140TolueneSolvent

Procedure

In a reactor fitted with a Dean-Stark apparatus hydroxymethyltrimethylsilane (3.8 g, 0.036 mol) and cyanoacetic acid (3.1 g, 0.036 mol) in 50 ml of toluene are refluxed for 4 hours in the presence of one drop of concentrated sulfuric acid. The organic phase is washed twice with water and is dried over sodium sulfate. It is concentrated under reduced pressure. Distillation under vacuum (b.p. 80° C. under 0.4 hPa) gives 4.3 g (69% yield) of trimethylsilanylmethyl cyanoacetate in the form of a colorless liquid which is used as it is in the following step.

Workup

  1. washThe organic phase is washed twice with water
  2. dry with materialis dried over sodium sulfate
  3. concentrationIt is concentrated under reduced pressure
  4. distillationDistillation under vacuum (b.p. 80° C. under 0.4 hPa)

Sources & evidence

ORD record
ord-72b9d66141084e9cb79733955ef87d74
Source dataset
uspto-grants-2007_06
Patent number
US07229609B2

Reaction notes

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