Water → 1-Hexylcycloprop-1-ene

HRID 840061Notes

Reaction equation

HRID 840061 reaction equation
Br[C:2]1(Br)[CH2:4][C:3]1(Br)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C[Li].O>C(OCC)C>[CH2:5]([C:3]1[CH2:4][CH:2]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 226216761,1,2-Tribromo-2-hexyl-cyclopropaneHCID 178418348HCID 178418348, compound

Product 1

HCID 226216521-Hexylcycloprop-1-eneYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.01 g (0.00278 mol) of 1,1,2-tribromo-2-hexyl-cyclopropane in 4 ml of diethyl ether was placed under a nitrogen atmosphere via use of a Firestone valve. While cooling in an ice water bath, 6.3 ml (0.00835 mol) of 1.4M methyl lithium in diethyl ether was added slowly by syringe. After 15 minutes, 2 ml of water was added via syringe. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo with a bath temperature under 20° C. to yield 0.300 g (87% of theoretical) of 1-hexyl-cyclopropene pure as an oil.

Workup

  1. temperatureWhile cooling in an ice water bath
  2. customThe resulting mixture was transferred to a separatory funnel
  3. customthe phases were separated
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed from the filtrate in vacuo with a bath temperature under 20° C.

Sources & evidence

ORD record
ord-26c0b651f1384c988b24009e56c91f96
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

Loading…