Ethyl 8-bromooctanoate → HCID 54540689, compound

HRID 346240Notes

Reaction equation

HRID 346240 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]Br)[CH3:2].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:18]1[C:14](=[O:24])[C:15]2[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:17]1=[O:19])[CH3:2]

Participants

4

Reactant 2

HCID 264813Ethyl 8-bromooctanoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 54540689HCID 54540689, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 26.4 g (0.1 mole) of ethyl-8-bromooctanoate (95%, Pfaltz and Bauer) and 19.6 g (0.1 mole) of potassium phthalimide (98%, Aldrich) in 250 mL of dimethylformamide was stirred and heated at reflux for 4 hr. The solvent was evaporated under reduced pressure and the viscous residue was partitioned between ethyl ether and water (400 mL each). The aqueous layer was further extracted with two 200 mL of ethyl ether. The combined ether extracts were washed with 200 mL of water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the viscous, oily residue was triturated with ethyl ether-petroleum ether (30°-60° C.) and the resulting solid was collected by filtration. The filtrate was evaporated under reduced pressure to give 25.2 g (79%) of crude title compound as a viscous oil. A 2.0 g sample of this oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPak® 500 silica; ethyl acetate-hexanes, 1:20; flow rate: 200 mL/min.). Fractions containing title compound were combined and the solvents were evaporated under reduced pressure to give 1.9 g (95% recovery) of clear liquid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hr
  3. customThe solvent was evaporated under reduced pressure
  4. customthe viscous residue was partitioned between ethyl ether and water (400 mL each)
  5. extractionThe aqueous layer was further extracted with two 200 mL of ethyl ether
  6. washThe combined ether extracts were washed with 200 mL of water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe viscous, oily residue was triturated with ethyl ether-petroleum ether (30°-60° C.)
  10. filtrationthe resulting solid was collected by filtration
  11. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2082408048f04127a182dd7c67c1ab97
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

Loading…