Dimethylformamide → 4-(2-Propen-1-yloxy)-9H-carbazole

HRID 2194295Notes

Reaction equation

HRID 2194295 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[OH:12][C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[CH2:26](Br)[CH:27]=[CH2:28]>O>[CH2:28]([O:12][C:13]1[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=[CH:15][CH:14]=1)[CH:27]=[CH2:26]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 1042514-Hydroxycarbazole

Product 1

HCID 595717514-(2-Propen-1-yloxy)-9H-carbazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

138 g of potassium carbonate was added to N,N-dimethylformamide (500 mL) solution of 121.9 g of 4-hydroxycarbazole. Under stirring, 88.6 g of allyl bromide was added thereto and the reaction mixture was stirred at 80° C. for 5 hours. The reaction mixture was allowed to cool, 3.5 L of water was added thereto, and extracted twice with 1 L of ethyl acetate. The combined organic layer was washed with 1 L of brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo. The residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:1), and 129 g of the subject compound was prepared.

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for 5 hours
  2. temperatureto cool
  3. extractionextracted twice with 1 L of ethyl acetate
  4. washThe combined organic layer was washed with 1 L of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by NH silica gel chromatography (ethyl acetate:n-hexane=1:1), and 129 g of the subject compound
  9. customwas prepared

Sources & evidence

ORD record
ord-7f37c059ffb7469f9722cc452593dff3
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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