Potassium Hydroxide → 1-Hydroxy-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

HRID 877462Notes

Reaction equation

HRID 877462 reaction equation
[F:1][C:2]([F:37])([C:7]1([O:32][Si](C)(C)C)[C:19]2[N:18](S(C3C=CC(C)=CC=3)(=O)=O)[C:17]3[C:12](=[CH:13][C:14]([C:30]#[N:31])=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1)[C:3]([F:6])([F:5])[F:4].[OH-].[K+]>C1COCC1.O>[OH:32][C:7]1([C:2]([F:37])([F:1])[C:3]([F:4])([F:5])[F:6])[C:19]2[NH:18][C:17]3[C:12](=[CH:13][C:14]([C:30]#[N:31])=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86676823HCID 86676823, compound

Product 1

HCID 529475461-Hydroxy-1-(perfluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrileYield 40.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(perfluoroethyl)-9-tosyl-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (180 mg, 0.3 mmol) in THF (5 mL), KOH (90 mg, 1.6 mmol) in H2O (1 mL) was added. The reaction mixture was refluxed for 20 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 residue which was purified by column chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound as a white solid (40 mg, 40%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.5 (bs, 1H), 7.9 (s, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.44 (d, J=7.5 Hz, 1H), 2.90-2.86 (m, 1H), 2.74-2.56 (m, 1H), 2.56 (s, 1H), 2.33-2.29 (m, 1H), 2.20-2.12 (m, 2H), 2.04-2.03 (m, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 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 residue which
  6. customwas purified by column chromatography [EtOAc-hexane (1:19) as eluant]

Sources & evidence

ORD record
ord-df864dabd347437f95b14a08aff6b950
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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