Acetone → HCID 22603584, compound

HRID 2307951Notes

Reaction equation

HRID 2307951 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+].CC(C)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:19]([N:6]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][C:9]([O:16][CH3:17])=[CH:10][CH:11]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 180AcetoneHCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 123393992,7-Dimethoxy-9H-carbazole

Product 1

HCID 22603584HCID 22603584, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A 50 mL flask was charged with 3.00 g (13.2 mmol) of compound 12, 5.10 g (26.4 mmol, Aldrich Co.) of 1-bromooctane, 1.06 g (26.4 mmol) of sodium hydroxide reagent grade, 134 mg (0.39 mmol) of tetrabutylamonium hydrogensulfate (TBAH) and 25 mL of anhydrous acetone. The resulting mixture was refluxed under argon for 24 h and then poured into 100 mL of distillated water. The aqueous layer was extracted three times with diethyl ether. The combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, 5% ethyl acetate in hexanes as eluent) to provide 4.06 g of the title product as white fluffy solid. M.P. 63-64° C. (Yield: 91%).

Workup

  1. temperatureThe resulting mixture was refluxed under argon for 24 h
  2. extractionThe aqueous layer was extracted three times with diethyl ether
  3. dry with materialThe combined organic fractions were dried over magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, 5% ethyl acetate in hexanes as eluent)

Sources & evidence

ORD record
ord-b7006aab6e2e48378608fa6a552911d3
Source dataset
uspto-grants-2004_12
Patent number
US06833432B2

Reaction notes

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