Potassium Acetate → HCID 68423402, compound

HRID 1965916Notes

Reaction equation

HRID 1965916 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.[C:19]([O-:22])(=[O:21])[CH3:20].[K+]>CN(C=O)C>[C:19]([O:22][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 517044Potassium AcetateHCID 139067719-(4-Bromobutyl)-9H-carbazole

Product 1

HCID 68423402HCID 68423402, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Compound 8 (40.1 g, 0.133 mol) and potassium acetate (19.5 g, 1.99 mol) were mixed in 300 mL of DMF under an argon atmosphere. The reaction mixture was stirred for 12 hours at 110° C. The organic phase was separated and extracted with ethyl acetate. The collected organics were then combined and dried over Na2SO4 and filtered. The solvent was evaporated to give the crude product. The resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:30 v/v) to yield 35 g (93%) of 4-(9H-carbazol-9-yl)butyl acetate (Compound 9).

Workup

  1. customThe organic phase was separated
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto give the crude product
  7. customThe resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:30 v/v)

Sources & evidence

ORD record
ord-173f7b90a9644e908c31424bdb0bbb08
Source dataset
uspto-grants-2013_04
Patent number
US08420231B2

Reaction notes

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