Methyl iodide → HCID 54073603, compound

HRID 1660160Notes

Reaction equation

HRID 1660160 reaction equation
[C:1]([O-])(C)(C)C.[K+].CI.[CH2:9]([O:11][C:12](=[S:18])[CH2:13][C:14]([CH2:16][CH3:17])=[O:15])[CH3:10]>O1CCCC1>[CH2:9]([O:11][C:12](=[S:18])[CH:13]([CH3:1])[C:14]([CH2:16][CH3:17])=[O:15])[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 53655223HCID 53655223, compound

Product 1

HCID 54073603HCID 54073603, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

First 12.3 g (0.11 mol) of potassium tert.-butanolate and then 15.6 g (0.11 mol) of methyl iodide were added to a solution of 17.6 g (0.1 mol) of 4-methylthioacetoacetic acid ethyl ester in 100 ml of tetrahydrofuran, while cooling. The mixture was subsequently stirred at 60° C. for 12 hours, the solvent was then distilled off in vacuo, 200 ml of methylene chloride were added to the residue and the solution was extracted by shaking twice with 100 ml of water each time. The organic phase was dried over sodium sulphate and evaporated in vacuo. The residue was distilled in vacuo. 14 g (74% of theory) of 2-methyl-4-methylthioacetoacetic acid ethyl ester with a boiling point of 95°-99° C./2 mm Hg were thus obtained. ##STR6##

Workup

  1. temperaturewhile cooling
  2. distillationthe solvent was then distilled off in vacuo, 200 ml of methylene chloride
  3. additionwere added to the residue
  4. extractionthe solution was extracted
  5. stirringby shaking twice with 100 ml of water each time
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customevaporated in vacuo
  8. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-2fa8896017b740c7bba2f770464a2822
Source dataset
uspto-grants-1981_12
Patent number
US04307107

Reaction notes

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