Ethanol → HCID 53356863, compound

HRID 877478Notes

Reaction equation

HRID 877478 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:34])([F:33])[F:32])([O:26][Si](C)(C)C)[C:8]([F:36])([F:35])[CH2:7][CH2:6][C:5]2=1.[OH-].[K+].CCO>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:32])([F:33])[F:34])([OH:26])[C:8]([F:35])([F:36])[CH2:7][CH2:6][C:5]2=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 87377375HCID 87377375, compound

Product 1

HCID 53356863HCID 53356863, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6,7-dichloro-2,2-difluoro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.090 g, 0.2 mmol) in THF (5 mL), cooled to 0° C., KOH (0.064 g, 1.0 mmol) in H2O (2 mL), was added and the reaction mixture was slowly cooled to room temperature and stirred for an additional 30 min EtOH (2 mL) was added to the reaction mixture and stirred at 80° C. for 4 h, diluted with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by column chromatography [EtOAc-hexane (3:17) as eluant] to give the title compound (0.025 g, 31%). 1H NMR (500 MHz, CDCl3, in ppm) 8.26 (bs, 1H), 7.63 (s, 1H), 7.52 (s, 1H), 3.31 (d, J=3.5 Hz, 1H), 2.97-2.94 (m, 2H), 2.61-2.52 (m, 2H).

Workup

  1. additionwas added to the reaction mixture
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude compound which
  6. customwas purified by column chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record
ord-cb0a511ce4634665808e9e2403ae502d
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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