Hexane → HCID 59331083, compound

HRID 2195593Notes

Reaction equation

HRID 2195593 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH3:27])[CH:8]=2)[CH3:2].[CH3:29][C:30](C)([O-:32])C.[K+].CCCCCC>C(OCC)(=O)C>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([C:16](=[O:18])[CH2:17][C:30](=[O:32])[CH3:29])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[C:7]([C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[CH3:27])[CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 8058Hexane2×HCID 23665647Potassium tert-butoxideHCID 59012247HCID 59012247, compound

Product 1

HCID 59331083HCID 59331083, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent3×

Procedure

A one liter four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser, and a thermometer was charged with 74.69 g of 1-[9-ethyl-6-(4-fluoro-2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, 538.66 g of ethyl acetate, and 67.33 g of potassium t-butoxide, and the mixture was refluxed in a nitrogen atmosphere for 1 hour. The reaction mixture was cooled to room temperature, and the white solid thus precipitated was collected by filtration by suction and washed with 500 ml of ethyl acetate. The resulting solid was stirred in 500 ml of 2N hydrochloric acid and 1.5 liters of ethyl acetate. The organic phase was washed with water until neutral. The organic phase was separated, dried with 70 g of magnesium sulfate, and filtered by suction. The solvent was removed by evaporation to give a pale yellow solid. The solid was dissolved in 150 ml of ethyl acetate and refluxed, and 100 ml of n-hexane was added thereto, followed by cooling to room temperature for crystallization. The filtrate was dissolved in 50 ml of ethyl acetate, refluxed, and 100 ml of n-hexane was added, followed by cooling to room temperature for crystallization. The resulting crystals were combined, collected by filtration by suction, and dried under reduced pressure to give 8.52 g (21%) of white crystals, which had a melting point of 132° C. and was identified by various analyses to be β-diketone compound No. 2 having a carbazolyl group.

Workup

  1. customA one liter four-necked flask equipped with a stirrer, a nitrogen inlet tube, a reflex condenser
  2. temperaturethe mixture was refluxed in a nitrogen atmosphere for 1 hour
  3. customthe white solid thus precipitated
  4. filtrationwas collected by filtration by suction
  5. washwashed with 500 ml of ethyl acetate
  6. washThe organic phase was washed with water until neutral
  7. customThe organic phase was separated
  8. dry with materialdried with 70 g of magnesium sulfate
  9. filtrationfiltered by suction
  10. customThe solvent was removed by evaporation
  11. customto give a pale yellow solid
  12. temperaturerefluxed
  13. temperatureby cooling to room temperature for crystallization
  14. temperaturerefluxed
  15. temperatureby cooling to room temperature for crystallization
  16. filtrationcollected by filtration by suction
  17. customdried under reduced pressure

Sources & evidence

ORD record
ord-ece06204ac0d4812b38dc56d820b1108
Source dataset
uspto-grants-2012_12
Patent number
US08338081B2

Reaction notes

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