Diethyl Ether → HCID 57803068, compound

HRID 2102687Notes

Reaction equation

HRID 2102687 reaction equation
[CH:1]1([Mg]Br)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCOCC.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19](=[O:25])[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1>O1CCCC1>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)([OH:25])[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2413316-Chloroindoline-2,3-dioneHCID 178419651HCID 178419651, compound

Product 1

HCID 57803068HCID 57803068, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-25 °C

Procedure

A solution of cyclohexyl magnesium bromide in ether (2.0 M, 3.10 mL, 6.25 mmol) (Aldrich) was added dropwise to a suspension of 6-chloroisatin (0.45 g, 2.5 mmol) (Crescent) in tetrahydrofuran (12.5 mL) with cooling in a −25° C. bath and magnetic stirring at such a rate that reaction temperature was kept below −10° C. Cooling bath was then removed and mixture was allowed to warm to room temperature. After stirring for an additional 2 hours, 15% aqueous ammonium chloride solution (12.5 mL) was added and mixture was extracted with ethyl acetate. Ethyl acetate layers were then washed with water, brine, combined, dried (Na2SO4), filtered and concentrated. Residue was stirred in dichloromethane at room temperature for 30 minutes and filtered to give crude rac-6-chloro-3-cyclohexyl-3-hydroxy-1,3-dihydro-indol-2-one as an off-white powder. (Yield 0.28 g, 43%).

Workup

  1. customthat reaction temperature
  2. customwas kept below −10° C
  3. temperatureCooling bath
  4. customwas then removed
  5. temperatureto warm to room temperature
  6. stirringAfter stirring for an additional 2 hours
  7. addition15% aqueous ammonium chloride solution (12.5 mL) was added
  8. extractionmixture was extracted with ethyl acetate
  9. washEthyl acetate layers were then washed with water, brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. stirringResidue was stirred in dichloromethane at room temperature for 30 minutes
  14. filtrationfiltered

Sources & evidence

ORD record
ord-b8c98201bddf4aea96771d6eebc6f381
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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