18-Crown-6 → HCID 54041294, compound

HRID 1107819Notes

Reaction equation

HRID 1107819 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([C:18]2[NH:22][C:21]([CH3:23])=[C:20]([CH3:24])[CH:19]=2)=[O:17])=[CH:10][CH:9]=1.C1OCCOCCOCCOCCOCCOC1.Br[CH2:44][CH:45]=[CH:46][CH3:47]>O1CCCC1>[CH2:44]([N:22]1[C:18]([C:16](=[O:17])[CH2:15][CH2:14][C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)=[CH:19][C:20]([CH3:24])=[C:21]1[CH3:23])[CH:45]=[CH:46][CH3:47]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 1224142-Butene, 1-bromo-HCID 18785698HCID 18785698, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 54041294HCID 54041294, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.82 g (0.00731 mole) of potassium tert-butoxide was added to a solution of 1.39 g (0.00567 mole) of 5-[3-(4-fluorophenyl)propionyl]-2,3-dimethylpyrrole and 0.19 g (0.00074 mole) of 18-crown-6 in 40 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 20 minutes. 1.80 g (0.0115 mole) of 1-bromo-2-butene (a mixture of cis and trans isomers) were added to the mixture and stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into ice-water and the aqueous mixture was extracted twice with 80 ml each of ethyl acetate. The extract was wahed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography through silica gel using a 1:10 mixture of ethyl acetate and hexane as an eluent to give 0.90 g of the title compound (cis/trans=22/78) as a pale yellow oil.

Workup

  1. additionwere added to the mixture
  2. stirringstirred at room temperature for 4 hours
  3. customAfter completion of the reaction
  4. extractionthe aqueous mixture was extracted twice with 80 ml each of ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography through silica gel using
  8. additiona 1:10 mixture of ethyl acetate and hexane as an eluent

Sources & evidence

ORD record
ord-3a74f07fb7814adb86d3037774e8a266
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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