Triethylamine → Oct-6-en-2-one

HRID 1196680Notes

Reaction equation

HRID 1196680 reaction equation
Br[CH:2]([CH3:6])[C:3](Br)=[O:4].[CH:7]1[CH2:12]CC=[CH:9][CH:8]=1.[CH2:13](N(CC)CC)C>CCCCCC>[CH3:12][CH:7]=[CH:8][CH2:9][CH2:6][CH2:2][C:3](=[O:4])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 116051,3-CyclohexadieneHCID 79047Propanoyl bromide, 2-bromo-

Product 1

HCID 537566Oct-6-en-2-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

81.3 g (0.38 mol) of 2-bromopropionyl bromide in 100 ml of hexane were added over a period of 1 hour to 39.8 g (0.5 mol) of 1,3-cyclohexadiene and 38.6 g (0.38 mol) of triethylamine while maintaining the temperature below 40° C. by occasional cooling. After an additional 3 hours at room temperature the precipitated triethylamine hydrobromide was removed by filtration. The filtrate was evaporated and the residue was purified by distillation under reduced pressure and subsequently by chromatography on silica gel using 4% diethyl ether in hexane for the elution. There were obtained 9.48 g of exo-8-bromo-8-methylbicyclo[4:2:0]oct-2-en-7-one and 5 89 g of endo-8-bromo-8-methylbicyclo[4:2:0]oct-2-en-7-one.

Workup

  1. temperaturewhile maintaining the temperature below 40° C. by occasional cooling
  2. customAfter an additional 3 hours at room temperature the precipitated triethylamine hydrobromide was removed by filtration
  3. customThe filtrate was evaporated
  4. distillationthe residue was purified by distillation under reduced pressure and subsequently by chromatography on silica gel using 4% diethyl ether in hexane for the elution

Sources & evidence

ORD record
ord-971ba7a98c114ed6b3adce0b7294d1b7
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

Loading…