Triethylamine → HCID 20354852, compound

HRID 372121Notes

Reaction equation

HRID 372121 reaction equation
C([O:4][C:5]1[CH2:9][CH2:8][CH2:7][C:6]=1[CH2:10][CH2:11][CH:12]([O:18][C:19](=[O:21])[CH3:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=O)C.BrBr.C(N(CC)CC)C>C(Cl)(Cl)(Cl)Cl>[C:19]([O:18][CH:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10][C:6]1[C:5](=[O:4])[CH2:9][CH2:8][CH:7]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 20354840HCID 20354840, compound

Product 1

HCID 20354852HCID 20354852, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a stirred solution of 1-acetoxy-2-(3-acetoxyoctyl)cyclopent-1-ene (59.2 g.) [prepared as described in (e) above] in dry carbon tetrachloride (350 ml.) was added dropwise, during 30 minutes, a solution of bromine (32 g.) in dry carbon tetrachloride (100 ml.) at -10° to -5° C. The solution was stirred for a further 20 minutes without cooling. Triethylamine (22.2 g.) was then added and the resulting mixture stirred and refluxed for 90 minutes. The mixture was filtered, and the filtrate washed with aqueous 2N sodium carbonate and with water. After drying over magnesium sulphate and evaporation of the solvent in vacuo, the residue was distilled, in the presence of a few crystals of potassium acetate, at 132°-168° C./0.25 mm.Hg, to give crude 2-(3-acetoxyoctyl)cyclopent-2-enone. This was redistilled, with potassium acetate, at 116°-135° C./0.15 mm.Hg to give 2-(3-acetoxyoctyl)cyclopent-2-enone (28.7 g.), nD28 = 1.470.

Workup

  1. customat -10° to -5° C
  2. temperaturewithout cooling
  3. stirringthe resulting mixture stirred
  4. temperaturerefluxed for 90 minutes
  5. filtrationThe mixture was filtered
  6. washthe filtrate washed with aqueous 2N sodium carbonate and with water
  7. dry with materialAfter drying over magnesium sulphate and evaporation of the solvent in vacuo
  8. distillationthe residue was distilled, in the presence of a few crystals of potassium acetate, at 132°-168° C./0.25 mm.Hg
  9. customto give crude 2-(3-acetoxyoctyl)cyclopent-2-enone
  10. distillationThis was redistilled, with potassium acetate, at 116°-135° C./0.15 mm.Hg

Sources & evidence

ORD record
ord-061ab31a3ae045abaa353198e9a47027
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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