HCID 18548204, compound → 1-(alpha,alpha-Dimethylbenzyl)-cyclopropene

HRID 1265978Notes

Reaction equation

HRID 1265978 reaction equation
[CH3:1][C:2]([C:10]1(Cl)[CH2:12][C:11]1(Br)Br)([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Li]>C(OCC)C>[CH3:9][C:2]([C:10]1[CH2:11][CH:12]=1)([CH3:1])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 18548204HCID 18548204, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 185482061-(alpha,alpha-Dimethylbenzyl)-cyclopropeneYield 121.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into a 50 ml flask equipped with a stirbar and septum and under an atmosphere of dry nitrogen was added 1.73 g (4.9 mmol) of 1-(α,α-dimethylbenzyl)-1-chloro-2,2-dibromocyclopropane and 12 ml of diethyl ether. After cooling in an ice bath for 10 minutes, 9.0 ml (12.6 mmol) of 1.4 M methyllithium in diethyl ether was added via syringe. A precipitate formed immediately. After stirring for 10 minutes the reaction was quenched with 3 ml of water. The aqueous layer was removed and the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo with the bath temperature at +25° C. yielding 0.94 g of 1-(α,α-dimethylbenzyl)-cyclopropene.

Workup

  1. customInto a 50 ml flask equipped with a stirbar and septum and under an atmosphere of dry nitrogen
  2. temperatureAfter cooling in an ice bath for 10 minutes
  3. customA precipitate formed immediately
  4. customwas quenched with 3 ml of water
  5. customThe aqueous layer was removed
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. customevaporated in vacuo with the bath temperature at +25° C.

Sources & evidence

ORD record
ord-e3fbb410bbf745a4acafd6ab15d36f0a
Source dataset
uspto-grants-2003_04
Patent number
US06548448B2

Reaction notes

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