Potassium tert-butoxide → Ethyl 3-ethenyl-1,2,2-trimethylcyclopropane-1-carboxylate

HRID 359178Notes

Reaction equation

HRID 359178 reaction equation
Br[CH2:2][CH:3]=[CH:4][C:5]([CH3:14])([CH3:13])[CH:6]([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].CC(C)([O-])C.[K+]>O1CCCC1>[CH3:12][C:6]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([CH3:14])([CH3:13])[CH:4]1[CH:3]=[CH2:2]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxide2×HCID 54437039Ethyl 6-bromo-2,3,3-trimethylhex-4-enoate

Product 1

HCID 13279169Ethyl 3-ethenyl-1,2,2-trimethylcyclopropane-1-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 526 mg (2 mmoles) of ethyl 6-bromo-2,3,3-trimethyl-4-hexenoate in 2 ml of anhydrous tetrahydrofuran was added dropwise to a suspension of 224 mg (2 mmoles) of potassium t-butoxide in 10 ml of tetrahydrofuran. The mixture was heated under reflux for two hours and then allowed to cool to room temperature. An additional 116 mg (1 mmole) of potassium t-butoxide was added, and the mixture again heated under reflux for two hours. The reaction mixture was poured into ice water, and the aqueous mixture extracted with diethyl ether. The ether extract was dried over magnesium sulfate and distilled to give 200 mg (55% yield) of ethyl 1,3,3-trimethyl-2-vinylcyclopropanecarboxylate, b.p. 92°-95°/1.5 mm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for two hours
  3. temperaturethe mixture again heated
  4. temperatureunder reflux for two hours
  5. extractionthe aqueous mixture extracted with diethyl ether
  6. extractionThe ether extract
  7. dry with materialwas dried over magnesium sulfate
  8. distillationdistilled

Sources & evidence

ORD record
ord-1525a0a5d16f467f89316b58897d34ab
Source dataset
uspto-grants-1991_03
Patent number
US04999451

Reaction notes

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