Hydrochloric Acid → 3-[2-(benzyloxy)phenyl]-3-hydroxy-3,5,6,7-tetrahydrocyclopenta[f]indol-2(1H)-one

HRID 490143Notes

Reaction equation

HRID 490143 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[NH:17]1[C:25]2[C:20](=[CH:21][C:22]3[CH2:28][CH2:27][CH2:26][C:23]=3[CH:24]=2)[C:19](=[O:29])[C:18]1=[O:30].Cl>C(OCC)C.C(OCC)(=O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1([OH:29])[C:20]2[C:25](=[CH:24][C:23]3[CH2:26][CH2:27][CH2:28][C:22]=3[CH:21]=2)[NH:17][C:18]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 5462224MagnesiumHCID 22560824Cyclopent[f]indole-2,3-dione, 1,5,6,7-tetrahydro-

Product 1

HCID 690608763-[2-(benzyloxy)phenyl]-3-hydroxy-3,5,6,7-tetrahydrocyclopenta[f]indol-2(1H)-oneYield 37%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Several drops of a 6 mL diethyl ether solution of 5.3 g of 2-benzyloxybromobenzene were added to a suspension of 583 mg of magnesium in 2 mL of diethyl ether under a nitrogen atmosphere to initiate the reaction, after which the rest was gradually added dropwise at a rate at which heating reflux was maintained. Upon completion of the dropping, the reaction mixture was heated and refluxed for 2 hours in an oil bath, and then cooled to room temperature. A reagent prepared as above was gradually added dropwise under ice cooling and a nitrogen atmosphere to an 11 mL tetrahydrofuran solution of 1.5 g of 1,5,6,7-tetrahydrocyclopenta[f]indol-2,3-dione. Upon completion of the dropping, the temperature was raised to room temperature, and then the reaction mixture was stirred for 16 hours at that temperature. A 1 mol/L hydrochloric acid aqueous solution was poured into the reaction solution, and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate, and the drying agent was then filtered off and the solvent was distilled off under reduced pressure. The residue was refined by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/2; v/v) to obtain 1.10 g of the titled compound (colorless powder).

Workup

  1. customthe reaction
  2. additionafter which the rest was gradually added dropwise at a rate at which
  3. temperatureheating
  4. temperaturereflux
  5. temperaturewas maintained
  6. temperatureUpon completion of the dropping, the reaction mixture was heated
  7. temperaturerefluxed for 2 hours in an oil bath
  8. customA reagent prepared
  9. additionas above was gradually added dropwise under ice cooling
  10. temperatureUpon completion of the dropping, the temperature was raised to room temperature
  11. washThe organic layer was washed with water and saturated brine
  12. dry with materialdried with magnesium sulfate
  13. filtrationthe drying agent was then filtered off
  14. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-68de799370d14a6990cf1d56869ced0e
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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