Potassium Hydroxide → HCID 53356866, compound

HRID 877491Notes

Reaction equation

HRID 877491 reaction equation
[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8]([C:22]([F:25])([F:24])[F:23])([O:17][Si](C)(C)C)[C:9]=1[NH:10]2.[OH-].[K+]>C1COCC1.O>[Cl:1][C:2]1[C:14]([Cl:15])=[C:13]([Cl:16])[CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8]([C:22]([F:25])([F:23])[F:24])([OH:17])[C:9]=1[NH:10]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 88914855HCID 88914855, compound

Product 1

HCID 53356866HCID 53356866, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5,6,7-Trichloro-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.11 g, 0.25 mmol) was dissolved in THF (5 mL) and a solution of KOH (0.050 g, 1 mmol) in water (5 mL) was added. The reaction mixture was stirred at room temperature for 1 h, diluted with water (10 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were dried over Na2SO4, concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography [EtOAc-hexane (1:9) as eluant] to furnish the title compound (0.09 g, 44%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.28 (bs, 1H), 7.42 (s, 1H), 3.29-3.23 (m, 1H), 3.02-2.95 (m, 1H), 2.44 (s, 1H), 2.26-2.22 (m, 1H), 2.09-1.98 (m, 3H).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was purified by silica gel column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record
ord-9d587a5a9c434455860cf33e5bd3a05b
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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