Potassium Hydroxide → 6,7-Dichloro-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-ol

HRID 877461Notes

Reaction equation

HRID 877461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11](S(C1C=CC(C)=CC=1)(=O)=O)[C:10]1[C:9]([C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33])([O:26][Si](C)(C)C)[CH2:8][CH2:7][CH2:6][C:5]2=1.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([C:31]([F:36])([F:37])[C:32]([F:33])([F:34])[F:35])([OH:26])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 87377499HCID 87377499, compound

Product 1

HCID 529450016,7-Dichloro-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-olYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 6,7-Dichloro-1-(perfluoroethyl)-9-tosyl-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.25 g, 0.47 mmol) in THF (5 mL) was added 6N KOH (6 mL). The reaction mixture was stirred at room temperature for 10 min. and then refluxed for 36 h, diluted with water and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude product which was purified by silica gel chromatography [EtOAc-hexane (3:22) as eluant] to give the title compound as a white solid (0.06 g, 34%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.21 (bs, 1H), 7.62 (s, 1H), 7.49 (s, 1H), 2.82-2.80 (m, 1H), 2.68-2.62 (m, 1H), 2.45 (s, 1H), 2.28-2.23 (m, 1H), 2.18-2.15 (m, 1H), 2.12-2.06 (m 1H), 2.03-2.0 (m, 1H).

Workup

  1. temperaturerefluxed for 36 h
  2. extractionextracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product which
  6. customwas purified by silica gel chromatography [EtOAc-hexane (3:22) as eluant]

Sources & evidence

ORD record
ord-057cd04548e845e6be6c66e603d91b60
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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