2,3-Dimethyl-2-butene → Ethyl 2,2,3,3-tetramethylcyclopropane-carboxylate

HRID 434753Notes

Reaction equation

HRID 434753 reaction equation
[CH3:1][C:2](=[C:4]([CH3:6])[CH3:5])[CH3:3].[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>>[CH3:1][C:2]1([CH3:3])[C:4]([CH3:6])([CH3:5])[CH:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 112502,3-Dimethyl-2-butene2×HCID 12192Ethyl diazoacetate

Product 1

HCID 136614Ethyl 2,2,3,3-tetramethylcyclopropane-carboxylate

Procedure

The method of Mesheheryakov, Chem. Abstr., 54, 24436d (1960) was employed. To a mixture of 19 g. (0.226 mole) of 2,3-dimethyl-2-butene and 2 g. of cupric sulfate is added at reflux a mixture of 51 g. (0.447 mole) ethyl diazoacetate and 19 g. of 2,3-dimethyl-2-butene. The resulting mixture is heated at reflux for 3 hours, cooled, filtered and distilled to afford 19.8 g. (26%) of the desired cyclic ester, B.P. 76°-77° (15 mm.).

Workup

  1. additionTo a mixture of 19 g
  2. temperatureat reflux
  3. additiona mixture of 51 g
  4. temperatureThe resulting mixture is heated
  5. temperatureat reflux for 3 hours
  6. temperaturecooled
  7. filtrationfiltered
  8. distillationdistilled
  9. customto afford 19.8 g

Sources & evidence

ORD record
ord-a395d2e5d0a745a991f9f24cb05b07fa
Source dataset
uspto-grants-1983_08
Patent number
US04399163

Reaction notes

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