Water → HCID 18674684, compound

HRID 1636073Notes

Reaction equation

HRID 1636073 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:3]1[C:4]2[NH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][C:2]=1[O:1][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 935512-HydroxycarbazoleHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 18674684HCID 18674684, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxycarbazole (0.5 g, 2.7 mmol), ethyl 6-bromohexanoate (0.6 g, 2.7 mmol), and potassium carbonate (0.4 g, 3.0 mmol) in dimethyl formamide (10 ml) were heated to 120° C. for 24 h. Water was added and extraction with ethyl acetate was performed. The combined organic phases were washed with water and dried (sodium sulfate). The solvent was removed i. vac. and the residue was purified by column chromatography (silica gel, ethyl acetate: heptane=1:1) to give ethyl 6-(9H-carbazol-2 yloxy)-hexanoate (290 mg, 33%) as a colorless solid. MS (M−H+)324.

Workup

  1. extractionextraction with ethyl acetate
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (sodium sulfate)
  4. customThe solvent was removed i
  5. customand the residue was purified by column chromatography (silica gel, ethyl acetate: heptane=1:1)

Sources & evidence

ORD record
ord-84156458377f4cacb27e5c5176e5995a
Source dataset
uspto-grants-2003_01
Patent number
US06512123B2

Reaction notes

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