3-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-fluoro-1H-indole → 4-(5-Fluoro-1H-indol-3-YL)cyclohexanone

HRID 1275538Notes

Reaction equation

HRID 1275538 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=4)[NH:12][CH:11]=3)[CH2:6][CH2:5]2)[O:3]C1>O1CCCC1.Cl>[F:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[C:10]2[CH:7]1[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]1

Participants

3

Reactant 1

HCID 105643253-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-fluoro-1H-indole

Product 1

HCID 107046834-(5-Fluoro-1H-indol-3-YL)cyclohexanoneYield 91%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 4-(5-fluoro-1H-3-indolyl)-cyclohexanone ethylene ketal (2.8 g, 0.01 mol) in 200 ml (1:1) tetrahydrofuran-hydrochloric acid (1N) was allowed to stir at room temperature for 16 hours. The mixture was concentrated to half volume. The aqueous was extracted with ethyl acetate. The organic extracts were washed with brine, dried (anhydrous sodium sulfate), and filtered. The crude product was purified by flash chromatography (40% ethyl acetate in hexane) to afford 2.1 g (91%) of product as yellow solid: mp 112-114° C.

Workup

  1. concentrationThe mixture was concentrated to half volume
  2. extractionThe aqueous was extracted with ethyl acetate
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. filtrationfiltered
  6. customThe crude product was purified by flash chromatography (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c15af7a53da9485b9b9b54abf1ce079e
Source dataset
uspto-grants-2000_12
Patent number
US06162803

Reaction notes

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